Novel Synthesis of α-Acetylstyrylphosphonates

Ryozo Sakoda; Hiroo Matsumoto; Kiyotomo Seto

doi:10.1055/s-1993-25926

Synthesis 1993; 1993(7): 705-713
DOI: 10.1055/s-1993-25926

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Novel Synthesis of α-Acetylstyrylphosphonates

Ryozo Sakoda^* , Hiroo Matsumoto, Kiyotomo Seto

^*Central Research Institute, Nissan Chemical IND., LTD., Tsuboi 722-1, Funabashi, Chiba, 274, Japan

Abstract

PDF Download All articles of this category

α-Acetylstyrylphosphonates were conveniently synthesized from 2-oxopropylphosphonates and substituted (dimorpholinomethyl)-benzenes (aminals). 4-Benzylidenemorpholinium carboxylates, generated from aminals by the action of α-halo acids, reacted with the phosphonates to give the products by elimination of the amine. The yields were influenced by the nature of substituents and their position in the phenyl ring and could be improved by adjustment of the acidities of the reacted acids. α-Acetylstyrylphosphonates containing various substituents on every position (at the 2-, 3-, or 4-position) in the phenyl ring were obtained generally in excellent yields using monochloroacetic acid.

PDF (786 kb)