Addition of phenylisocyanate to 3, 5-diphenyl-1, 2-dithiolium-4-olate gives a thioketone. Issue 14 (5th April 2017)

• Record Type: Journal Article
• Authors: Probert, Michael R.; Ramsden, Christopher A.; Stanforth, Stephen P.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 14(2017)
• Page Start: 1425
• Page End: 1427
• Publication Date: 2017-04-05
• Subjects: Mesomeric betaine -- Mesoionic -- Semi-conjugated; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.02.076
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The reaction of phenylisocyanate with a mesoionic heterocycle produces a novel thioketone. The structures of products from similar reactions to that above have been either corrected or confirmed. X-ray crystallography and spectral data confirm the thioketone structure. Abstract: The Type B mesoionic heterocycle, 3, 5-diphenyl-1, 2-dithiolium-4-olate, reacts with phenylisocyanate producing a thioketone derivative rather than a pseudo-semi-conjugated heterocyclic mesomeric betaine. The structure of the thioketone product was confirmed by an X-ray crystallographic investigation.