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Preparation of ring‐labelled adamantane derivatives. I. 2‐adamantanecarboxylic acid‐2‐ 14 C and 2‐methyladamantane‐2‐ 14 C
Author(s) -
Majerski Z.,
Wolf A. P.,
Schleyer P. V. R.
Publication year - 1970
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590060210
Subject(s) - adamantane , diazomethane , chemistry , ring (chemistry) , stereochemistry , carboxylic acid , cyclobutene , medicinal chemistry , organic chemistry
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).