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Preparation of ring-labelled adamantane derivatives. I. 2-adamantanecarboxylic acid-2-14C and 2-methyladamantane-2-14C

✍ Scribed by Z. Majerski; A. P. Wolf; P. V. R. Schleyer

Publisher
John Wiley and Sons
Year
1970
Tongue
French
Weight
436 KB
Volume
6
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A relatively simple route to 2‐substituted adamantane derivatives labelled with ^14^C at the 2‐position in the adamantane skeleton was developed. The approach used (Figure I) involved ring expansion of adamantanone by labelled diazomethane, conversion of the resulting 4‐homoadamantanone (II) to diazoketone IV, followed by photolytic Wolff ring contraction to 2‐adamantanecarboxylic acid‐2‐^14^C (VI). Reduction of the carboxylic acid by conventional procedures gave 2‐methyladamantane‐2‐^14^C (IX).

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