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RESEARCH FRONT
Contents Vol 63(12)

Thioketenes and Iminopropadienethiones RN=C=C=C=S from Isoxazolones

David Kvaskoff A and Curt Wentrup A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

B Corresponding author. Email: wentrup@uq.edu.au

Australian Journal of Chemistry 63(12) 1694-1702 https://doi.org/10.1071/CH10340
Submitted: 14 September 2010  Accepted: 5 October 2010   Published: 6 December 2010

Abstract

Isoxazolones 6 undergo thermal elimination of propene and isopropylthiol to produce thioketenes 7 at 500–600°C under flash vacuum thermolysis conditions. At 700–900°C further fragmentation occurs to produce iminopropadienethiones, RNCCCS 8. In addition, 3-alkylisoxazolones 6d–e rearrange to cyanothioketenes 10d–e. Compounds 7, 8, and 10 were characterized by Ar matrix IR spectroscopy and comparison with density functional theory-calculated spectra. Thioketenes 7 reacted with amines to afford thioamides 11. Reaction of aryliminopropadienethiones 8 with amines caused cyclization to 2-aminoquinoline-4(1H)-thiones 16.


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