ACID-CATALYZED CONDENSATION OF 1,3-BENZENEDITHIOL WITH ALDEHYDES - A LOW DILUTION PREPARATION OF 1,3,10,12-TETRATHIA[3.3]METACYCLOPHANES

Authors
BEER PD DREW MGB IBBOTSON A LACY SM
Citation
Pd. Beer et al., ACID-CATALYZED CONDENSATION OF 1,3-BENZENEDITHIOL WITH ALDEHYDES - A LOW DILUTION PREPARATION OF 1,3,10,12-TETRATHIA[3.3]METACYCLOPHANES, Tetrahedron, 53(9), 1997, pp. 3155-3166
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
9
Year of publication
1997
Pages
3155 - 3166
Database
ISI
SICI code
0040-4020(1997)53:9<3155:ACO1WA>2.0.ZU;2-F
Abstract
The condensation of 1,3-benzenedithiol with aliphatic aldehydes and fe rrocenecarboxaldehyde under acid catalysis in ethanol gave ubstituted- 1,3,10,12-tetrathia[3.3]metacyclophanes in poor to moderate yield. Eac h isolated macrocycle was found to consist of two geometric isomers, t he proportions of which varied with each aldehyde used. Variable tempe rature NMR studies confirmed the extreme flexibility of the (R = Me) s ystem, which crystallises mainly as the cis isomer. (C) 1997 Elsevier Science Ltd.