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Acid-catalysed condensation of 1,3-benzenedithiol with aldehydes: A low dilution preparation of 1,3,10,12-tetrathia[3.3]metacyclophanes

✍ Scribed by Paul D. Beer; Michael G.B. Drew; Arthur Ibbotson; Stephen M. Lacy

Book ID: 104207608
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 534 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00026-4

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✦ Synopsis

The condensation of 1.3-benzenedithiol with aliphatic aldehydes and ferrocenecarboxaldehyde under acid catalysis in ethanol gave 2,11 -disubstituted-1,3, I 0,12-tetrathia[3.3]metacyclophanes in poor to moderate yield. Each isolated macrocycle was found to consist of two geometric isomers, the proportions of which varied with each aldehyde used. Variable temperature NMR studies confirmed the extreme flexibility of the (R = Me) system, which crystallises mainly as the cis isomer.

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