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Addition of phenylisocyanate to 3,5-diphenyl-1,2-dithiolium-4-olate gives a thioketone

DOI: 10.1016/j.tetlet.2017.02.076 DOI Help

Authors: Michael R. Probert (Newcastle University) , Christopher A. Ramsden (Keele University) , Stephen P. Stanforth (University of Northumbria)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Tetrahedron Letters

State: Published (Approved)
Published: February 2017
Diamond Proposal Number(s): 6749

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.

Journal Keywords: Mesomeric betaine; Mesoionic; Semi-conjugated

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

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