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Synthesis and properties of new macrocyclic compounds: Utilization of bond character of hypervalent sulfur in tetraazathiapentalene derivatives

✍ Scribed by Noboru Matsumura; Ryuji Hirase; Shigeki Kamitani; Yasuyuki Okumura; Kazuhiko Mizuno

Publisher: Journal of Heterocyclic Chemistry
Year: 2005
Tongue: English
Weight: 232 KB
Volume: 42
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570420621

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✦ Synopsis

2,3-Bis [(p-isothiocyanatomethylphenyl)methyl]-6,7-dihydro-5H-2a-thia(2a-S IV )-2,3,4a,7a-tetraazacyclopent[cd]indene-1,4(2H,3H)-dithione (3), prepared by the reaction of 2,3-dimethyl-6,7-dihydro-5H-2athia(2a-S IV )-2,3,4a,7a-tetraazacyclopent-[cd]indene-1,4(2H,3H)-dithione (1) with p-xylylene diisothiocyanate, reacted with N,N'-dialkyl substituted diamines to give macrocyclic compounds bearing hypervalent sulfur by a ring closure reaction in good yields. These macrocyclic compounds were converted into ringexpanded macrocyclic compounds with release of the hypervalent sulfur by treating with NaBH 4 and CF 3 COOH.

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