NaNO2 Mediated Difunctionalizations of Alkenes for the Synthesis of β-Oximino Phosphorodithioates

doi:10.6023/cjoc202508016

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 515-522.DOI: 10.6023/cjoc202508016 Previous Articles Next Articles

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亚硝酸钠介导烯烃双官能化合成β-肟基二硫代磷酸酯

何卫保^a, 贺梦云^a, 廖琼^a, 易荣楠^b^,^*()

^a 湖南化工职业技术学院技术与职业教育研究中心湖南株洲 412000
^b 湖南警察学院食药环及毒品检验技术湖南省普通高等学校重点实验室长沙 410138

收稿日期:2025-08-17 修回日期:2025-09-24 发布日期:2025-11-05
通讯作者: 易荣楠
基金资助:
长沙市自然科学基金(104872); 湖南化工职业技术学院博士科研启动基金资助项目

NaNO₂ Mediated Difunctionalizations of Alkenes for the Synthesis of β-Oximino Phosphorodithioates

Weibao He^a, Mengyun He^a, Qiong Liao^a, Rongnan Yi^b^,^*()

^a Research Center for Technical and Vocational Education Studies, Hunan Chemical Vocational Technology College, Zhuzhou, Hunan 412000
^b Key Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138

Received:2025-08-17 Revised:2025-09-24 Published:2025-11-05
Contact: Rongnan Yi
Supported by:
Natural Science Foundation of Changsha City(104872); Scientific Research Foundation for Ph.D. Scholars of Hunan Chemical Vocational Technology College

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Abstract

NaNO₂ mediated difunctionalization of alkenes with P₄S₁₀ and alcohols has been developed for the construction of β-oximino phosphorodithioates. This reaction utilizes NaNO₂ as the oxime source to effectively synthesize various β-oximino phosphorodithioates under mild conditions. The method features the advantages of simple operation, mild condition, and non metal-pollution. Preliminary mechanistic studies suggest that this reaction occurs through the NO positive ion process.

Key words: sodium nitrite, difunctionalizations of alkene, P₄S₁₀, β-oximino phosphorodithioate

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Weibao He, Mengyun He, Qiong Liao, Rongnan Yi. NaNO₂ Mediated Difunctionalizations of Alkenes for the Synthesis of β-Oximino Phosphorodithioates[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 515-522.

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亚硝酸钠介导烯烃双官能化合成β-肟基二硫代磷酸酯

NaNO₂ Mediated Difunctionalizations of Alkenes for the Synthesis of β-Oximino Phosphorodithioates

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Entry	Additive	Solvent (V∶V)	T/℃	Yield^b/%
1	HBF₄ (1 equiv.)	EtOH/DMSO (1∶5)	25	52
2	HCl (1 equiv.)	EtOH/DMSO (1∶5)	25	53
3	H₂SO₄ (1 equiv.)	EtOH/DMSO (1∶5)	25	43
4	FeCl₃ (10 mol%)	EtOH/DMSO (1∶5)	25	41
5	CuCl₂ (10 mol%)	EtOH/DMSO (1∶5)	25	42
6	—	EtOH/DMSO (1∶5)	25	54
7	—	EtOH/DCE (1∶5)	25	51
8	—	EtOH/CHCl₃ (1∶5)	25	52
9	—	EtOH/CH₂Cl₂ (1∶5)	25	50
10	—	EtOH/DMF (1∶5)	25	29
11	—	EtOH/THF (1∶5)	25	47
12	—	EtOH/1,4-dioxane (1∶5)	25	46
13	—	EtOH/Toluene (1∶5)	25	42
14	—	EtOH/DMSO (1∶1)	25	54
15	—	EtOH/DMSO (1∶3)	25	55
16	—	EtOH/DMSO (1∶8)	25	58
17	—	EtOH/DMSO (1∶10)	25	63
18	—	EtOH/DMSO (1∶19)	25	42
19	—	EtOH	25	36
20	—	EtOH/DMSO (1∶10)	40	72
21	—	EtOH/DMSO (1∶10)	65	86
22	—	EtOH/DMSO (1∶10)	80	82
23	—	EtOH/DMSO (1∶10)	65	71^c
24	—	EtOH/DMSO (1∶10)	65	59^d