烯基膦酸酯：在霍纳-沃兹沃思-埃蒙斯条件下，用甲基 2-[(二乙氧基膦酰基)甲基]苯甲酸酯反应得到的意外产物。

Alkenylphosphonates: unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner-Wadsworth-Emmons conditions.

机构信息

School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New Zealand.

出版信息

Org Biomol Chem. 2011 Jun 21;9(12):4432-5. doi: 10.1039/c1ob05506b. Epub 2011 May 16.

Abstract

Methyl 2-[(diethoxyphosphoryl)methyl]benzoate reacts with several aldehydes to produce an alkenylphosphonate as the major product, together with varying amounts of the expected Horner-Wadsworth-Emmons product, a 1,2-disubstituted E-alkene. Use of a bulky aldehyde or the tert-butyl ester favours the normal HWE product.

摘要

2-[(二乙氧基膦酰基)甲基]苯甲酸甲酯与几种醛反应，主要生成烯基膦酸酯，同时还生成一定量的预期的霍纳-沃兹沃思-埃蒙斯产物，即 1,2-二取代的 E-烯烃。使用大位阻醛或叔丁酯有利于生成正常的 HWE 产物。