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Synthesis and Some Reactions of 2,4,6-Cycloheptatrienethione

✍ Scribed by Harry A. Dugger; André S. Dreiding

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
549 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of 2,4,6‐cycloheptatrienethione (1) was accomplished by reaction of tropone and phosphorus pentasulfide. Although 1 proved to be extremely unstable in concentrated solution, its UV. spectrum was measured, the ε‐values being determined indirectly by hydrolysis to tropone. The proof of structure rests on analytical data, conversion to tropone oxime on reaction with hydroxylamine and reaction with the sodium salt of malonitrile to give 2‐amino‐3‐cyano‐3a__H__‐cyclohepta[b]thiophene (4) which rearranged on chromatography to give what is probably the corresponding 8__H__‐compound (5). On dissolving 1 in 95% sulfuric acid, a large hypsochromic shift in the UV. spectrum was observed, which may be due to the mercaptotropylium ion.

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