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Réaction de quelques amides substitués de l'acide benzénephosphosphoneux avec les α‐halogénococétones
Author(s) -
Hudson R. F.,
Chopard P. A.,
Salvasri G.
Publication year - 1964
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19640470229
Subject(s) - chemistry , alkylation , methanol , medicinal chemistry , benzaldehyde , phosphonium , chloride , alcohol , amine gas treating , phosphonate , hydrochloride , ketone , ethanol , phenacyl , organic chemistry , catalysis
Bis‐dimethylaminophenylphosphine reacts with α‐halogeno esters and ketones to give hygroscopic quaternary phosphonium salts, leading to ill‐defined betaines which readily undergo the W ITTIG reaction with benzaldehyde. In alcohol solution, the reaction with phenacyl chloride gives the corresponding ketone, dialkyl phenyl‐phosphonate and amine hydrochloride. A mixture of trimethylammonium and tetra‐methylammonium chloride has been obtained from methanol, but dimethylammonium chloride only from ethanol. These observations are interpreted by a bimolecular (S N 2) de‐alkylation of a trimethoxyphosphonium intermediate in methanol, and a unimolecular (S N 1) de‐alkylation of the corresponding triethoxyphosphonium intermediate in ethanol.