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Synthesis and Some Reactions of 2,4,6‐Cycloheptatrienethione
Author(s) -
Dugger Harry A.,
Dreiding André S.
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590305
Subject(s) - chemistry , tropone , hypsochromic shift , hydroxylamine , sulfuric acid , hydrolysis , dissolution , medicinal chemistry , organic chemistry , physics , quantum mechanics , fluorescence
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.