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Preparation of ring labelled adamantane derivatives II. 2-adamantanone-2−14C, adamantane-2−14C and 1-methyladamantane-2 or 4−14C

✍ Scribed by Samuel H. Liggero; Zdenko Majerski; Paul von R. Schleyer; A. P. Wolf; C. S. Redvanly; Hans Wynberg; J. A. Boerma; J. Strating

Publisher
John Wiley and Sons
Year
1971
Tongue
French
Weight
368 KB
Volume
7
Category
Article
ISSN
0022-2135

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✦ Synopsis

A high-yield, relatively simple synthetic route leading to incorporation of l'C into the secondary position of the adamantane nucleus is described. The synthesis was achieved by the sequence shown in Figure 2. The key steps involved the introduction of a I4C label by diazome1hane-14C ring expansion of adamantanone to give 4-hom0adamantanone-4-~~C ( I ) . Benzylic acid rearrangement of the corresponding homoadamantane diketone ( I l ) gave hydroxy acid ( I l l ) which was converted by a novel reaction (SOClzlbenzene) to 2-adamantanone-2-~4C ( I V ) . The overall yield of labelled 2-adamantanone was 66 "/,. Wolff-Kishner reduction of ( I V ) gave ~damantane-2-~4C ( V ) . This was converted to the I-methyl derivative ( V l l ) by treatment of the corresponding bromide ( V I ) with methylmagnesium bromide.

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