亚磺酸内酯研究进展

doi:10.6023/A23100435

摘要/Abstract

亚磺酸内酯化合物是一类有趣且重要的含硫杂环化合物, 在医药、生物和材料科学方面具有重要的研究价值和应用潜力, 也是有机合成中的关键中间体之一. 由于合成方法的不足, 此类化合物长久被忽视, 发展缓慢, 近期亚磺酸内酯重新引起了关注. 因此, 对亚磺酸内酯的合成方法、性能以及应用进行了系统的概述. 最后, 对亚磺酸内酯的发展现状进行总结和展望, 以期为亚磺酸内酯的未来发展提供参考.

关键词: 亚磺酸内酯, 合成, 性能, 应用

Heterocycles are a highly valuable class of complex scaffolds that are involved in a various kind of well-known organic compounds of industrial and pharmacological importance. Sultine, an important class of sulfur-containing heterocyclic compounds, plays central roles in medicine, biology and material science. The sulfur atom in sultine is located at a vertex of a stable pyramid without identical substituents, making it a chiral center with potential applications in asymmetric synthesis. The asymmetry of sultine can be easily eliminated by oxidizing it into sultone. In addition, sultines have shown to be versatile intermediates in organic synthesis. They can act as useful synthons with hidden bifunctionality: opening the heterocycle at the S—O bond leads to the simultaneous appearance of two functional groups in the product. Despite their potential, the chemical research of sultines have been long neglected and underdeveloped due to their inaccessibility. Only recently, some research groups have discovered protocols for the preparation of these heterocycles and explored their properties using methods such as visible light-induced radical homolytic substitution cyclization and radical polar crossover cyclization, and so on. It is worth noting that although sultines have been discussed in a few reviews, they are not systematic but very fragmentary. Owing to the increasing interest in studies on sultines and their transformations. The synthesis methods, physical properties and applications of sultines are systematically summarized in the past 130 years. The synthetic tactics are reviewed by highlighting their product diversity, selectivity and applicability, along with the mechanistic rationale where possible. Additionally, the chemical transformations of sultines, including photolysis, thermolysis, ring-opening reactions, oxidation/reduction reactions, and rearrangement reactions, are demonstrated. The usefulness of sultines in synthesis, medicine and materials is described as well. Finally, the development status of sultine compounds is reviewed, and a future perspective is provided, in order to offer reference for researchers engaged in sultine chemistry.

Key words: sultine, synthesis, property, application

引用此文

杨铃悦, 李赟婷, 舒超. 亚磺酸内酯研究进展[J]. 化学学报, 2024, 82(2): 171-189.

Lingyue Yang, Yunting Li, Chao Shu. Research Progress on Sultine[J]. Acta Chimica Sinica, 2024, 82(2): 171-189.

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图/表 64

图1. 亚磺酸内酯化学

Figure 1. Sultine chemistry

图2. Rongalite参与的亚磺酸内酯的合成

Figure 2. Rongalite involved the synthesis of sultines

图3. 二卤-邻二甲苯的阴离子接力环化

Figure 3. Anion relay cyclization of dihalogen-o-xylene

图4. DBU介导的亲核取代环化反应

Figure 4. DBU-mediated nucleophilic substitution cyclization

图5. 亲核取代环化反应合成亚磺酸内酯B和D

Figure 5. Nucleophilic substitution cyclization for the synthesis of sultine B and D

图6. 羟基亚磺酸环化合成亚磺酸内酯

Figure 6. Cyclization of hydroxysulfinates to sultine

图7. 羟基亚砜的环化合成亚磺酸内酯

Figure 7. Cyclization of hydroxysulfoxides to sultine

图8. α,β-不饱和-γ-亚磺酸内酯的合成

Figure 8. Synthesis of α,β-unsaturated γ-sultine

图9. 炔丙醇参与的α,β-不饱和-γ-亚磺酸内酯的合成

Figure 9. Synthesis of α,β-unsaturated γ-sultine from propargyl alcohol

图10. 不饱和键参与的亲电环化反应

Figure 10. Electrophilic cyclization on unsaturated bonds

图11. Friedel-Crafts环化反应

Figure 11. Friedel-Crafts cyclization

图12. 苯并亚磺酸内酯的合成

Figure 12. Synthesis of benzo-fused sultine

图13. 自由基均相取代合成γ-亚磺酸内酯

Figure 13. Synthesis of γ-sultine by radical homolytic substitution

图14. 光催化苯并亚磺酸内酯的合成

Figure 14. Photocatalyzed synthesis of benzo-fused sultines

图15. 光催化合成苯并亚磺酸内酯推测反应机理

Figure 15. Proposed mechanism of photocatalysed synthesis of benzo-fused sultines

图16. 光催化合成氟甲基化亚磺酸内酯

Figure 16. Photocatalyzed synthesis of fluoromethylated sultines

图17. 氟甲基化亚磺酸内酯的推测反应机理

Figure 17. Proposed reaction mechanism of fluoromethylated sultine

图18. 多环亚磺酸内酯的合成

Figure 18. Synthesis of polycyclic sultine

图19. 能量转移供能的亚磺酸内酯合成

Figure 19. Energy transfer powered synthesis of sultines

图20. 能量转移催化推测机理

Figure 20. Proposed mechanism of energy transfer catalysis

图21. 二溴取代的亚磺酸内酯合成

Figure 21. Synthesis of dibromo substituted sultine

图22. 电催化合成亚磺酸内酯

Figure 22. Electrocatalyzed synthesis of sultines

图23. 自由基重排产生亚磺酸内酯

Figure 23. Synthesis of sultine via radical rearrangement

图24. 氧化反应合成亚磺酸内酯

Figure 24. Synthesis of sultine via oxidation

图25. m-CPBA氧化合成亚磺酸内酯

Figure 25. Synthesis of sultine by m-CPBA oxidation

图26. NaIO4氧化合成亚磺酸内酯

Figure 26. Synthesis of sultine by NaIO4 oxidation

图27. LiAlH4还原产生亚磺酸内酯

Figure 27. Synthesis of sultine via LiAlH4 reduction

图28. β-磺内酯还原反应

Figure 28. β-Sultone reduction

图29. 扩环合成亚磺酸内酯

Figure 29. Synthesis of sultine by ring expansion

图30. 碱催化扩环合成亚磺酸内酯

Figure 30. Synthesis of sultine by ring expansion under base conditions

图31. 缩环合成亚磺酸内酯

Figure 31. Synthesis of sultine by contraction

图32. 重排合成亚磺酸内酯

Figure 32. Synthesis of sultine by rearrangement

图33. 重排合成亚磺酸内酯B

Figure 33. Synthesis of sultine B by rearrangement

图34. SO2参与的环加成反应-1

Figure 34. SO2 involved cycloaddition-1

图35. SO2参与的环加成反应-2

Figure 35. SO2 involved cycloaddition-2

图36. SO2参与的环加成反应-2

Figure 36. SO2 involved cycloaddition-2

图37. 通过其它策略合成亚磺酸内酯-1

Figure 37. The synthesis of sultines via other methods-1

图38. 四氯苯醌参与的亚磺酸内酯合成

Figure 38. Chloranil involved the synthesis of sultines

图39. 苯并亚磺酸内酯B合成

Figure 39. Synthesis of benzo-fused sultine B

图40. 通过其它策略合成亚磺酸内酯-2

Figure 40. The synthesis of sultines via other methods-2

图41. 单晶结构分析

Figure 41. X-ray crystallography analysis

图42. 亚磺酸内酯构型分析

Figure 42. Configuration analysis of sultine

图43. 单烯烃参与的Diels-Alder环加成反应

Figure 43. Mono-olefin mediated Diels-Alder cycloaddition reaction

图44. 1,3-丁二烯参与的Diels-Alder环加成反应

Figure 44. 1,3-Butadiene mediated Diels-Alder cycloaddition reaction

图45. β-亚磺酸内酯分解

Figure 45. Decomposition of β-sultine

图46. β,γ-不饱和六元亚磺酸内酯热解反应

Figure 46. Thermolysis of β,γ-unsaturated sultine

图47. 双环亚磺酸内酯热分解反应

Figure 47. Decomposition of cyclopropane fused sultine

图48. 二苯并亚磺酸内酯A的热解反应

Figure 48. Thermolysis of dibenzoxathiine oxide A

图49. 苯并亚磺酸内酯A的热解反应

Figure 49. Thermolysis of benzofused sultine A

图50. 亚磺酸内酯A和E的光解反应

Figure 50. Photolytic decomposition of the sultine A and E

图51. 多环亚磺酸内酯的紫外光解反应

Figure 51. UV light photolysis of sultine

图52. 亚磺酸内酯A的热解和光解反应

Figure 52. Thermolysis and photolysis of sultine A

图53. δ-亚磺酸内酯的光解反应

Figure 53. Photolytic decomposition of δ-sultine

图54. 亚磺酸内酯的水解反应

Figure 54. Alkaline hydrolysis of sultine

图55. 卤素离子参与的亚磺酸内酯开环反应

Figure 55. Cleavage of sultines by halide ions

图56. β-亚磺酸内酯醇解反应

Figure 56. Alcoholysis of β-sultine

图57. 有机金属试剂参与的开环反应

Figure 57. Organometallic reagents involved ring opening reactions

图58. 亚磺酸内酯的氧化反应

Figure 58. Oxidation of sultines

图59. 亚磺酸内酯的还原反应

Figure 59. Reduction reactions of sultines

图60. 亚磺酸内酯的重排反应

Figure 60. Rearrangement of sultine

图61. 亚磺酸内酯的应用-1

Figure 61. Application of sultine-1

图62. 亚磺酸内酯的应用-2

Figure 62. Application of sultine-2

图63. 亚磺酸内酯的应用-3

Figure 63. Application of sultine-3

图64. 亚磺酸内酯的应用-4

Figure 64. Application of sultine-4

参考文献 148

[1]	Zhang, Y.; Li, H.; Yang, X.; Zhou, P.; Shu, C. Chem. Commun. 2023, 59, 6272. doi: 10.1039/D3CC01238G
[2]	Bondarenko, O. B.; Saginava, L. G.; Zyk, N. V. Russ. Chem. Rev. 1996, 65, 147. doi: 10.1070/RC1996v065n02ABEH000204
[3]	Dittmer, D. C.; Hoey, M. D. In The Chemistry of Sulphinic Acids, Esters and their Derivatives, Chapter 9, Ed.: Patai, S., Wiley, Chichester, England, 1990, p. 239.
[4]	Zhu, Z.; Deng, Z.; Ouyang, X.; Shu, C. Synlett 2023, 34, 1943. doi: 10.1055/a-2080-5069
[5]	Jarvis, W. F.; Hoey, M. D.; Finocchio, A. L.; Dittmer, D. C. J. Org. Chem. 1988, 53, 5750. doi: 10.1021/jo00259a026
[6]	Baker, W.; Pant, C. M.; Stoodley, R. J. J. Chem. Soc., 1978, 668.
[7]	Knittel, D. Monatsh. Chem. 1982, 113, 37. doi: 10.1007/BF00814334
[8]	Harpp, D. N.; Gleason, J. G. Tetrahedron Lett. 1969, 1447.
[9]	Harpp, D. N.; Gleason, J. G.; As, D. K. J. Org. Chem. 1971, 36, 322. doi: 10.1021/jo00801a017
[10]	Harpp, D. N.; Gleason, J. G. J. Org. Chem. 1971, 36, 1314. doi: 10.1021/jo00808a038
[11]	Inoue, H.; lnoguchi, N.; Imoto, E. Bull. Chem. Soc. Jpn. 1977, 50, 197. doi: 10.1246/bcsj.50.197
[12]	Gaoni, Y. J. Org. Chem. 1981, 46, 4502. doi: 10.1021/jo00335a037
[13]	Hoey, M. D.; Dittmer, D. C. J. Org. Chem. 1991, 56, 1947. doi: 10.1021/jo00005a054
[14]	Hof, F.; Nuckolls, C.; Craig, S. L.; Martín, T.; Rebek, J. Jr. J. Am. Chem. Soc. 2000, 122, 10991. doi: 10.1021/ja002340q
[15]	Schmibt, A. H.; Kircher, G.; Willems, M. J. Org. Chem. 2000, 65, 2379. doi: 10.1021/jo9915877
[16]	Kotha, S.; Ganesh, T.; Ghost, A. K. Bioorg. Med. Chem. Lett. 2000, 10, 1755. pmid: 10937741
[17]	Wu, A.-T.; Liu, W.-D.; Chung, W.-S. J. Chin. Chem. Soc. (Taipei) 2002, 49, 77.
[18]	Kotha, S.; Khedkar, P. J. Org. Chem. 2009, 74, 5667. doi: 10.1021/jo900658z
[19]	Jia, J. Z.; Scarborough, R. M.; Zhang, P.; Halfon, S.; Arfsten, A. E.; Sinha, U.; Zhu, B.-Y. Chem. Pharm. Bull. 2009, 57, 1004. doi: 10.1248/cpb.57.1004
[20]	Meng, X.; Zhang, W.; Tan, Z.; Du, C.; Li, C.; Bo, Z.; Li, Y.; Yang, X.; Zhen, M.; Jiang, F.; Zheng, J.; Wang, T.; Jiang, L.; Shu, C.; Wang, C. Chem. Commun. 2012, 48, 425. doi: 10.1039/C1CC15508C
[21]	Meng, X.; Zhang, W.; Tan, Z.; Li, Y.; Ma, Y.; Wang, T.; Shu, C.; Wang, C. Adv. Funct. Mater. 2012, 22, 2187. doi: 10.1002/adfm.v22.10
[22]	Smith, G. M. T.; Burton, P. M.; Bray, C. D. Angew. Chem., Int. Ed. 2015, 54, 15236. doi: 10.1002/anie.v54.50
[23]	Charlton, J. L.; Durst, T. Tetrahedron Lett. 1984, 25, 5287.
[24]	Durst, T.; Charlton, J. L.; Mount, D. B. Can. J. Chem. 1986, 64, 246. doi: 10.1139/v86-042
[25]	Jung, F.; Molin, M.; Van Den Elzen, R.; Durst, T. J. Am. Chem. Soc. 1974, 63, 935.
[26]	Sharma, N. K.; de Reinach-Hirtzbach, F.; Durst, T. Can. J. Chem. 1976, 54, 3012. doi: 10.1139/v76-427
[27]	Breau, L.; Sharma, N. K.; Butler, J. R.; Durst, T. Can. J. Chem. 1991, 69, 185. doi: 10.1139/v91-029
[28]	Malwal, S. R.; Gudem, M.; Hazra, A.; Chakrapani, H. Org. Lett. 2013, 15, 1116. doi: 10.1021/ol400190f
[29]	Malwal, S. R.; Chakrapani, H. Org. Biomol. Chem. 2015, 13, 2399. doi: 10.1039/C4OB02466D
[30]	Thoumazean, E.; Jousseaume, B.; Tiffon, F.; Durboudin, J.-G. Heterocycles 1982, 19, 2247. doi: 10.3987/R-1982-12-2247
[31]	Von Rein, F. W.; Richey, H. G. J. Organomet. Chem. 1969, 20, 32.
[32]	Eisch, J. J.; Merkley, J. H. J. Organomet. Chem. 1969, 20, 27.
[33]	Welker, M. E. Chem. Rev. 1992, 92, 97. doi: 10.1021/cr00009a004
[34]	Scott, E. E.; Donnelly, E. T.; Welker, M. E. J. Organomet. Chem. 2003, 673, 67. doi: 10.1016/S0022-328X(03)00167-0
[35]	Franks, M. A.; Schrader, E. A.; Pietsch, E. C.; Pennella, D. R.; Torti, S. V.; Welker, M. E. Bioorg. Med. Chem. 2005, 13, 2221. doi: 10.1016/j.bmc.2004.12.037
[36]	Ying, M.; Smentek, M. G.; Ma, R.; Day, C. S.; Torti, S. V.; Welker, M. E. Lett. Org. Chem. 2009, 6, 242. doi: 10.2174/157017809787893064
[37]	Wang, M.; Jiang, X. Chem. Rec. 2021, 21, 3338. doi: 10.1002/tcr.v21.12
[38]	Zeng, D.; Wang, M.; Deng, W.-P.; Jiang, X. Org. Chem. Front. 2020, 7, 3956. doi: 10.1039/D0QO00987C
[39]	Smil, D. V.; Souza, F. E. S.; Fallis, A. G. Bioorg. Med. Chem. Lett. 2005, 15, 2057. doi: 10.1016/j.bmcl.2005.02.056
[40]	Dhami, K. S. Chem. Ind. (London) 1968, 1004.
[41]	Dhami, K. S. Indian J. Chem. 1974, 12, 278.
[42]	Henrick, K.; Johnson, B. L. Aust. J. Chem. 1972, 25, 2263.
[43]	Torosyan, M. A.; Mirzoyan, R. S.; Isakhanyan, S. S.; Arutyunyan, A. M. Arm. Khim. Zh. 1986, 39, 124(Chem. Abstr. 1987, 106, 138299).
[44]	Barbieri, W.; Bernardi, L.; Coda, S.; Vigevani, A. Tetrahedron Lett. 1971, 4913.
[45]	Hanson, G.; Kemp, D. S. J. Org. Chem. 1981, 46, 5441. doi: 10.1021/jo00339a048
[46]	Coulomb, J.; Certal, V.; Fensterbank, L.; Lacôte, E.; Malacria, M. Angew. Chem., Int. Ed. 2006, 45, 633. doi: 10.1002/anie.v45:4
[47]	Kyne, S. H.; Aitken, H. M.; Schiesser, C.; Lacôte, E.; Malacria, M.; Ollivier, C.; Fensterbank, L. Org. Biomol. Chem. 2011, 9, 3331. doi: 10.1039/c1ob05043e
[48]	Aiken, H. M.; Hancock, A. N.; Schiesser, C. H. Chem. Commun. 2012, 48, 8326. doi: 10.1039/c2cc33856d
[49]	Coulomb, J.; Certal, V.; Larraufie, M.-H.; Ollivier, C.; Corbet, J.-P.; Mignani, G.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. - Eur. J. 2009, 15, 10225. doi: 10.1002/chem.v15:39
[50]	Salaverri, A. F. N.; Maestro, M. C.; Alemán, J. Org. Lett. 2019, 21, 5295. doi: 10.1021/acs.orglett.9b01911
[51]	Pitzer, L.; Schwarz, J. L.; Glorius, F. Chem. Sci. 2019, 10, 8285. doi: 10.1039/c9sc03359a pmid: 32055300
[52]	Wiles, R. J.; Molander, G. A. Isr. J. Chem. 2020, 60, 281. doi: 10.1002/ijch.v60.3-4
[53]	Sharma, S.; Singh, J.; Sharma, A. Adv. Synth. Catal. 2021, 363, 3146. doi: 10.1002/adsc.v363.13
[54]	Li, H.; Zhang, Y.; Yang, X.; Deng, Z.; Zhu, Z.; Zhou, P.; Ouyang, X.; Yuan, Y.; Chen, X.; Yang, L.; Liu, M.; Shu, C. Angew. Chem., Int. Ed. 2023, 62, e202300159.
[55]	Zhang, Y.; Zhou, P.; Yang, X.; Li, H.; Deng, Z.; Ren, M.; Shu, C. Adv. Synth. Catal. 2023, 365, 3478. doi: 10.1002/adsc.v365.20
[56]	Deng, Z.; Zhu, Z.; Ru, Z.; Zou, X.; Ouyang, X.; Yang, X.; Zhou, P.; Tian, S.; Ma, X.; Song, R.; Sun, Q.; Lin, C.; Shu, C. ACS Catal. 2023, 13, 13232. doi: 10.1021/acscatal.3c03367
[57]	Kelley, C. J.; Carmack, M. Tetrahedron Lett. 1975, 16, 3605. doi: 10.1016/S0040-4039(00)91335-2
[58]	Knittel, D.; Kastening, B. J. Appl. Electrochem. 1973, 3, 291. doi: 10.1007/BF00613035
[59]	Kastening, B.; Gostisa-Mihelcic, B. J. Electroanal. Chem. 1979, 100, 801. doi: 10.1016/S0022-0728(79)80199-0
[60]	Knittel, D. Monatsch. Chem. 1982, 113, 37. doi: 10.1007/BF00814334
[61]	Dittmer, D. C.; Henion, R. S.; Takashina, N. J. Org. Chem. 1969, 34, 1310. doi: 10.1021/jo01257a023
[62]	Astrologes, G. W.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 4390. doi: 10.1021/ja00455a030
[63]	Davis, A. P.; Whitham, G. H. J. Chem. Soc. Chem. Commun. 1981, 741.
[64]	Block, E.; Wall, A. J. Org. Chem. 1987, 52, 809. doi: 10.1021/jo00381a020
[65]	Wolinsky, J.; Marhenke, R. L. J. Org. Chem. 1975, 40, 1766. doi: 10.1021/jo00900a019
[66]	Kohn, H.; Charumilind, P.; Simonsen, S. H. J. Am. Chem. Soc. 1979, 101, 5431. doi: 10.1021/ja00512a062
[67]	Kohn, H.; Charumilind, P. J. Org. Chem. 1980, 45, 4359. doi: 10.1021/jo01310a019
[68]	Martin, L. D.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 3511. doi: 10.1021/ja00452a059
[69]	Astrologes, G. W.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 4400. doi: 10.1021/ja00455a031
[70]	Nishio, T.; Shiwa, K.; Sakamoto, M. Helv. Chim. Acta 2002, 85, 2383. doi: 10.1002/1522-2675(200208)85:8【-逻辑与-】amp;lt;2383::AID-HLCA2383【-逻辑与-】amp;gt;3.0.CO;2-E
[71]	Kawęcki, R. Tetrahedron: Asymmetry 2003, 14, 2827.
[72]	Wolinsky, J.; Marhenke, R. L. J. Org. Chem. 1975, 40, 1766. doi: 10.1021/jo00900a019
[73]	Peters, R.; Koch, F. M. Synlett 2008, 1505.
[74]	Peters, R.; Koch, F. M. Chem. - Eur. J. 2011, 17, 3679. doi: 10.1002/chem.v17.13
[75]	Hoffmann, R. W.; Sieber, W. Justus Liebigs Ann. Chem. 1967, 703, 96. doi: 10.1002/jlac.v703:1
[76]	Dittmer, D. C.; Henion, R. S.; Takashina, N. 153rd National Meeting, American Chemical Society, Miami, Florida, 1967, Abstract O-101.
[77]	Dittmer, D. C.; Henion, R. S.; Takashina, N. J. Org. Chem. 1969, 34, 1310. doi: 10.1021/jo01257a023
[78]	Christl, M.; Brunn, E.; Lanzendorfer, F. J. Am. Chem. Soc. 1984, 106, 373. doi: 10.1021/ja00314a022
[79]	King, J. F.; Piers, K.; Piers, D. J. H.; Mc lntosh, C.; de Mayo, P. J. Chem. Soc., Chem. Commun. 1969, 31, 34.
[80]	King, J. F.; de Mayo, P.; McIntosh, C. L.; Piers, K.; Smith, D. J. H. Can. J. Chem. 1970, 48, 3704. doi: 10.1139/v70-619
[81]	Dittmer, D. C.; Nelsen, T. R. J. Org. Chem. 1976, 41, 3044. doi: 10.1021/jo00880a033
[82]	Hall, C. R.; Smith, D. J. H. Tetrahedron Lett. 1974, 3633.
[83]	Schuckmann, H. P.; Von Sonntag, C. J. Photochem. 1983, 22, 55. doi: 10.1016/0047-2670(93)80008-D
[84]	Dodson, R. M.; Hammen, P. D.; Davis, R. A. J. Chem. Soc., Chem. Commun. 1968, 9.
[85]	Dodson, R. M.; Hammen, P. D.; Davis, R. A. J. Org. Chem. 1971, 36, 2693. doi: 10.1021/jo00817a026
[86]	Dodson, R. M.; Hammen, P. D.; Fan, J. Y. J. Org. Chem. 1971, 36, 2703. doi: 10.1021/jo00817a028
[87]	King, J. F.; Huston, B. L.; Hawson, A.; Komery, J.; Deaken, D. M.; Harding, D. R. K. Can. J. Chem. 1971, 49, 936. doi: 10.1139/v71-153
[88]	King, J. F.; Hawson, A.; Huston, B. L.; Danks, L. J.; Komery, J. Can. J. Chem. 1971, 49, 943. doi: 10.1139/v71-154
[89]	King, J. F.; Hawson, A.; Deaken, D. M.; Komery, J. J. Chem. Soc., Chem. Commun. 1969, 33.
[90]	Kowalewski, R.; Margarethe, P. Angew. Chem., Int. Ed. 1988, 27, 1374.
[91]	Harpp, D. N.; Steliou, K.; Chan, T. H. J. Am. Chem. Soc. 1978, 100, 1222. doi: 10.1021/ja00472a032
[92]	Harpp, D. N.; Mullins, D. F. Can. J. Chem. 1983, 1, 757.
[93]	Heldeweg, R.; Hogeveen, H. J. Am. Chem. Soc. 1976, 98, 2341. doi: 10.1021/ja00424a060
[94]	Durst, T.; Tetreault-Ryan, L. Tetrahedron Lett. 1978, 2353.
[95]	De Lucchi, O.; Lucchini, V. J. Chem. Soc., Chem. Commun. 1982, 464.
[96]	Hogeveen, H.; Zwart, L. J. Am. Chem. Soc. 1982, 104, 4889. doi: 10.1021/ja00382a024
[97]	Cutler, A.; Fish, R. W.; Giering, W. P.; Rosenblum, M. J. Am. Chem. Soc. 1972, 94, 4354. doi: 10.1021/ja00767a060
[98]	Shabarov, Y. S.; Saginova, L. G.; Bondarenko, O. B. USSR SU 1209694 1986[Chem. Abstr. 1987, 106, p. 5002].
[99]	Saginova, L. G.; Bondarenko, O. B.; Shabarov, Y. S. J. Org. Chem. USSR, 1985, 21, 608.
[100]	Bondarenko, O. B.; Voevodskaya, T. I.; Saginova, L. G.; Tafeenko, V. A.; Shabarov, Y. S. J. Org. Chem. USSR 1987, 23, 1736.
[101]	Bohen, J. M.; Joullie, M. M. Tetrahedron Lett. 1971, 1815.
[102]	Bohen, J. M.; Joullie, M. M. J. Org. Chem. 1973, 38, 2652. doi: 10.1021/jo00955a017
[103]	Gruetzmacher, H.; Roesky, H. W. Chem. Ber. 1987, 120, 995. doi: 10.1002/cber.v120:6
[104]	Lichtenberg, D. W.; Wojcicki. A. J. Organomet. Chem. 1971, 33, C77. doi: 10.1016/S0022-328X(00)87408-2
[105]	Haszeldine, R. N.; Bannister, W. D.; Booth, B. L.; Loader, P. L. J. Chem. Soc. A 1971, 930.
[106]	Thomasson, J. E.; Robinson, P. W.; Ross, D. A.; Wojcicki, A. Inorg. Chem. 1971, 10, 2130. doi: 10.1021/ic50104a008
[107]	Kroll, J. O.; Wojcicki, A. J. Organomet. Chem. 1974, 66, 95. doi: 10.1016/S0022-328X(00)93892-0
[108]	Churchill, M. R.; Wormald, J.; Ross, D. A.; Thomasson, J. E.; Wojcicki, A. J. Am. Chem. Soc. 1970, 92, 1795. doi: 10.1021/ja00709a082
[109]	Braverman, S.; Reisman, D. J. Am. Chem. Soc. 1977, 99, 605. doi: 10.1021/ja00444a048
[110]	Braverman, S.; Reisman, D. Tetrahedron Lett. 1977, 1753.
[111]	Braverman, S.; Duar, Y. J. Am. Chem. Soc. 1983, 105, 1061. doi: 10.1021/ja00342a073
[112]	Veselovskaya, S. V.; Saginova, L. G.; Shabarov, Y. S. J. Org. Chem. USSR 1987, 23, 115.
[113]	Strating, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1967, 86, 641. doi: 10.1002/recl.v86:6
[114]	Bonini, B. F.; Maccagnani, G.; Mazzanti, G.; Thijs, L.; Ambrosius, H. P. M. M.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1977, 1468.
[115]	Bonini, B. F.; Maccagnani, G.; Mazzanti, G.; Pedrini, P.; Zwanenburg, B. Gazz. Chim. Ital. 1977, 107, 283.
[116]	Gaillard, S.; Papamicaël, C.; Dupas, G.; Marsais, F.; Levacher, V. Tetrahedron 2005, 61, 8138. doi: 10.1016/j.tet.2005.06.047
[117]	Givens, E. N.; Hamilton, L. A. J. Org. Chem. 1967, 32, 2857. doi: 10.1021/jo01284a045
[118]	Liskamp, R. M. J.; Zeegers, H. J. M.; Ottenheijm, H. C. J. J. Org. Chem. 1981, 46, 5408. doi: 10.1021/jo00339a034
[119]	Xi, Z.; Cheng, X.-F.; Chen, W.-B.; Cao, L.-Q. Tetrahedron Lett. 2006, 47, 3337. doi: 10.1016/j.tetlet.2006.03.089
[120]	Marson, C. M.; Giles, P. R. J. Org. Chem. 1995, 60, 8067. doi: 10.1021/jo00129a056
[121]	Haasnoot, C. A. G.; Liskamp, R. M. J.; van Dael, P. A. W.; Noordik, J. H.; Ottenheijm, H. C. J. J. Am. Chem. Soc. 1983, 105, 5406. doi: 10.1021/ja00354a037
[122]	Buchanan, G. W.; Sharma, N. K.; de Reinach-Hirtzbach, F.; Durst, T. Can. J. Chem. 1977, 55, 44. doi: 10.1139/v77-008
[123]	Markovic, D.; Roversi, E.; Scoppelliti, R.; Vogel, P; Meana, R.; Sordo, J. A. Chem. Eur. J. 2003, 9, 4911. doi: 10.1002/chem.v9:20
[124]	Roversi, E.; Scopelliti, R.; Solari, E.; Vogel, P.; Braa, P.; Menndez, B.; Sordo, J. A. Chem. Eur. J. 2002, 8, 1336. doi: 10.1002/(ISSN)1521-3765
[125]	Roversi, E.; Vogel, P. Helv. Chim. Acta 2002, 85, 761. doi: 10.1002/1522-2675(200203)85:3【-逻辑与-】amp;lt;761::AID-HLCA761【-逻辑与-】amp;gt;3.0.CO;2-Q
[126]	Jung, F.; Sharma, N. K.; Durst, T. J. Am. Chem. Soc. 1973, 95, 3420. doi: 10.1021/ja00791a078
[127]	Nokami, J.; Kunieda, N.; Kinoshita, M. Tetrahedron Lett. 1975, 16, 2179. doi: 10.1016/S0040-4039(00)72671-2
[128]	Durst, T.; Gimbarzevsky, B. P. J. Chem. Soc., Chem. Commun. 1975, 724.
[129]	Jung, F.; Molin, M.; Van Den Elzen, R.; Durst, T. J. Am. Chem. Soc. 1974, 63, 935.
[130]	Jung, F. J. Chem. Soc., Chem. Commun. 1976, 525.
[131]	Squires, T. G.; Venier, C. G.; Hodgson, B. A.; Chang, L. W.; Davis, F. A.; Panunto, T. W. J. Org. Chem. 1981, 46, 2373. doi: 10.1021/jo00324a031
[132]	Durst, T.; Finlay, J. D.; Smith, D. J. H. J. Chem. Soc., Perkin Trans. 1 1979, 1950.
[133]	Durst, T.; Huang, J. C.; Sharma, N. K. Can. J. Chem. 1978, 56, 512. doi: 10.1139/v78-082
[134]	Burger, U.; Gmunder, C.; Schmidlin, S.; Bernardinelli, G. Helv. Chim. Acta 1990, 73, 1724. doi: 10.1002/hlca.v73:6
[135]	King, J. F.; Mayo, P. D.; McIntosh, C. L.; Piers, K.; Smith, D. J. H. Can. J. Chem. 1970, 48, 3704. doi: 10.1139/v70-619
[136]	Harpp, D. N.; Vines, S. M.; Montillier, J. P.; Chan, T. H. J. Org. Chem. 1976, 41, 3987. doi: 10.1021/jo00887a012
[137]	Duboudin, J. G.; Jousseaume, B.; Thoumazeau, E. Bull. Soc. Chim. Fr. 1983, 105.
[138]	Xi, Z.; Cheng, X.-F.; Chen, W.-B.; Cao, L.-Q. Tetrahedron Lett. 2006, 47, 3337. doi: 10.1016/j.tetlet.2006.03.089
[139]	Givens, E. N.; Hamilton, L. A. J. Org. Chem. 1967, 32, 2857. doi: 10.1021/jo01284a045
[140]	Henrick, K.; Johnson, B. L. Aust. J. Chem. 1972, 25, 2263. doi: 10.1071/CH9722263
[141]	Chan, T. H.; Montillier, J. P.; van Horn, W. F.; Harpp, D. N. J. Am. Chem. Soc. 1970, 92, 7224. doi: 10.1021/ja00727a048
[142]	Dondoni, A.; Giorgianni, P.; Battaglia, A.; Andreetti, G. D. J. Chem. Soc., Chem. Commun. 1981, 350.
[143]	Torelli, V.; Philbert, D. Chem. Abstr. 1978, 89, 110126.
[144]	Torelli, V.; Philbert, D. Chem. Abstr. 1980, 93, 26659.
[145]	Yolka, S.; Dunach, E.; Loiseau, M.; Lizzani-Cuvelier, L.; Fellous, R.; Rochard, S.; Schippa, C.; George, G. Flavour Fragrance J. 2002, 17, 425. doi: 10.1002/ffj.v17:6
[146]	Pirkle, W. H.; Hoekstra, M. S. J. Am. Chem. Soc. 1976, 98, 1832. doi: 10.1021/ja00423a031
[147]	Ngamnithiporn, A.; Chuentragool, P.; Ploypradith, P.; Ruchirawat, S. Org. Lett. 2022, 24, 4192. doi: 10.1021/acs.orglett.2c01437
[148]	Katritzky, A. R.; Zhang, Z. Z.; Lang, H.; Jubran, N.; Leichter, L. M.; Sweeny, N. J. Mater. Chem. 1997, 57, 1399.