ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Bis-dimethylaminophenylphosphine reacts with α-halogeno esters and ketones to give hygroscopic quaternary phosphonium salts, leading to ill-defined betaines which readily undergo the WITTIG 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 (SN2) de-alkylation of a trimethoxyphosphonium intermediate in methanol, and a unimolecular (SN1) de-alkylation of the corresponding triethoxyphosphonium intermediate in ethanol.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19640470229
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