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Alkenylphosphonates: unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner–Wadsworth–Emmons conditions†
Lynton J. Baird,Cédric Colomban,Claire Turner,Paul H. Teesdale-Spittle,Joanne E. Harvey
Organic & Biomolecular Chemistry Pub Date : 05/16/2011 00:00:00 , DOI:10.1039/C1OB05506B
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.

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