H. Bredereck, G. Simchen, W. Griebenow
Nov 1, 1973
Citations
1
Influential Citations
26
Citations
Journal
Chemische Berichte
Abstract
Benzyltriphenylphosphonium-Salze (1) reagieren mit dem Aminal-tert-butylester 2 zu [α-(Dimethylaminomethylen)benzyl]triphenylphosphonium-Salzen (3) oder zu Ylenen, den Benzylidentriphenylphosphoranen (4). Die Hydrolyse von [α-(Dimethylaminomethylen)-4-methoxybenzyl]triphenylphosphonium-bromid-Tetrahydrat (3b · 4H2O) mit wasriger Kalilauge fuhrt unter Abspaltung von Benzol zu [α-(Dimethylaminomethylen)-4-methoxybenzyl]diphenylphosphinoxid (8). Mit Natriumathylat entstehen aus [α-(Dimethylaminomethylen)benzyl]triphenylphosphoniumbromid (3a) ω-(Dimethylamino)styrol (9) und Triphenylphosphinoxid. Orthoamides, XXV. Synthesis and Reactions of [α-(Dimethylaminomethylene)benzyl]triphenylphosphonium Salts Benzyltriphenylphosphonium salts (1) react with the aminal tert-butyl ester 2 to give [α-(dimethylaminomethylene)benzyl]triphenylphosphonium salts (3) or the corresponding ylenes, the benzylidenetriphenylphosphoranes (4). Hydrolysis of [α-(dimethylaminomethylene)-4-methoxybenzyl]triphenylphosphonium bromide tetrahydrate (3b · 4H2O) with aqueous potassium hydroxide results in elimination of benzene and formation of [α-(dimethylaminomethylene)-4-methoxybenzyl]diphenylphosphine oxide (8). Reaction of [α-(dimethylaminomethylene)benzyl]triphenylphosphonium bromide (3a) with sodium ethoxide affords ω-(dimethylamino)styrene (9) and triphenylphosphine oxide.