Chemistry and applications of phophonium and arsonium ylides XII. Reaction of p-nitrophenyl methylenetriphenylphosphorane and arsorane with methyl 2-perfluoroalkynoates and stereospecific synthesis of (Z) methyl 3-perfluoroalkyl-4-p-nitrophenyl-3-butenoat

Acta Chimica Sinica ›› 1991, Vol. 49 ›› Issue (3): 284-289. Previous Articles Next Articles

Original Articles

膦、胂叶立德的化学与应用 XII. 对硝基苯基亚甲基三苯基膦、胂与2-全氟炔酸甲酯的反应以及(Z)3-全氟烷基 4-对硝基苯基-3-丁烯酸甲酯的立体专一性合成

丁维钰;张平生;浦家齐;张春明;毛世高;王绮文;沈伟

上海科技大学;中国科学院上海有机化学研究所

发布日期:1991-03-15

Chemistry and applications of phophonium and arsonium ylides XII. Reaction of p-nitrophenyl methylenetriphenylphosphorane and arsorane with methyl 2-perfluoroalkynoates and stereospecific synthesis of (Z) methyl 3-perfluoroalkyl-4-p-nitrophenyl-3-butenoat

DING WEIYU;ZHANG PINGSHENG;PU JIAQI;ZHANG CHUNMING;MAO SHIGAO;WANG QIWEN;SHEN WEI

Published:1991-03-15

Abstract

Reaction of p-nitrobenzylphosphonium or -arsonium bromides with Me 2-perfluoroalkynoates in the presence of K2CO3 gave adducts Ph3P:C(CO2Me)CR:CHC6H4NO2-p (I; R = C3F7, CF3, C2F5) or mixtures of Ph3P:C(CO2Me)CR:CHC6H4CO2-p (II; same R) and Ph3P:C(C6H4NO2-p)CR:CHCO2Me (III; same R). The ratio of II to III was increased with an increase of reaction temperature, the formation of II being favored at higher temperature while at 90? the reaction gave II exclusively. The P-C bond cleavage occurred when II or III were heated in aqueous methanol in sealed tubes at 150? and Me (Z)-3-perfluoroalkyl-4-p-nitrophenyl-3-butenoates (IV) were formed stereospecifically. III could be transformed to II on heating. As-C bond cleavage occurred when I were heated in refluxing aqueous methanol and the same products were formed. The mechanism of hydrolysis was discussed.

Key words: INFRARED SPECTROPHOTOMETRY, ALKYNE, ELEMENTAL ANALYSIS, MASS SPECTROGRAPHY, NMR SPECTROMETRY, BROMIDE, NITROBENZENE, TRIPHENYLPHOSPHINE, METHYL ESTER, TRIPHENYL GROUP

CLC Number:

O627

Cite this article

DING WEIYU;ZHANG PINGSHENG;PU JIAQI;ZHANG CHUNMING;MAO SHIGAO;WANG QIWEN;SHEN WEI. Chemistry and applications of phophonium and arsonium ylides XII. Reaction of p-nitrophenyl methylenetriphenylphosphorane and arsorane with methyl 2-perfluoroalkynoates and stereospecific synthesis of (Z) methyl 3-perfluoroalkyl-4-p-nitrophenyl-3-butenoat[J]. Acta Chimica Sinica, 1991, 49(3): 284-289.

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膦、胂叶立德的化学与应用 XII. 对硝基苯基亚甲基三苯基膦、胂与2-全氟炔酸甲酯的反应以及(Z)3-全氟烷基 4-对硝基苯基-3-丁烯酸甲酯的立体专一性合成

Chemistry and applications of phophonium and arsonium ylides XII. Reaction of p-nitrophenyl methylenetriphenylphosphorane and arsorane with methyl 2-perfluoroalkynoates and stereospecific synthesis of (Z) methyl 3-perfluoroalkyl-4-p-nitrophenyl-3-butenoat

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