Helvetica chimica acta

Orthocarbonsäure??ester mit 2, 4, 10??Trioxaadamantanstruktur als Carboxylschutzgruppe; Verwendung zur Synthese von substituierten Carbonsäuren mit Hilfe von …

G Voss, H Gerlach

Index: Voss, Gundula; Gerlach, Hans Helvetica Chimica Acta, 1983 , vol. 66, # 7 p. 2294 - 2307

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Citation Number: 33

Abstract

Summary The surprising stability of 2, 4, lO-trioxa-3-adamantyl derivatives 1 against nucleophilic substitution by organomagnesium compounds is discussed and shown to be caused by unfavourable stereoelectronic and steric factors governing the substitution of these cage compounds (Scheme 2). As a consequence, a number of Grignard reagents 2 containing the carboxyl group masked as 2, 4, 10-trioxa-3-adamantyl group could be ...