Studies on the regioselectivity of the alkylation reaction of carbanions derived from nitroalkylphosphonates

Acta Chimica Sinica ›› 1993, Vol. 51 ›› Issue (10): 1016-1022. Previous Articles Next Articles

Original Articles

硝基烷基膦酸酯碳负离子烷基化反应区域选择性研究

张荣馀;陈坚;瞿建波

中国科学院上海有机化学研究所

发布日期:1993-10-15

Studies on the regioselectivity of the alkylation reaction of carbanions derived from nitroalkylphosphonates

ZHANG RONGYU;CHEN JIAN;QU JIANBO

Published:1993-10-15

Abstract

The reaction of dicarbanions derived from nitroalkylphosphonates with alkyl halides gave C-alkylation product. The regioselectivity of this reaction was depended on the structure of nitroalkylphosphonates. The reaction of dianion derived from a-nitroalkylphosphonates with alkyl halides afforded unique b-carbon-alkylation product. Whereas, with the dianion of b-nitroalkylphosphonates the alkylation reaction was occurred exclusively on the a-carbon atom adjacent to the phosphoryl group. Possible reaction mechanisms were discussed.

Key words: REACTION MECHANISM, PHOSPHONIC ACID ESTER, ALKYLATION, REGIOSELECTIVITY

CLC Number:

O627

Cite this article

ZHANG RONGYU;CHEN JIAN;QU JIANBO. Studies on the regioselectivity of the alkylation reaction of carbanions derived from nitroalkylphosphonates[J]. Acta Chimica Sinica, 1993, 51(10): 1016-1022.

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硝基烷基膦酸酯碳负离子烷基化反应区域选择性研究

Studies on the regioselectivity of the alkylation reaction of carbanions derived from nitroalkylphosphonates

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