[4+3] Cycloaddition of Donor–Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho‐Bisthioquinone. Issue 2 (4th December 2015)

• Record Type: Journal Article
• Authors: Garve, Lennart K. B.; Pawliczek, Martin; Wallbaum, Jan; Jones, Peter G.; Werz, Daniel B.
• Is Part Of: Chemistry. Volume 22:Issue 2(2016)
• Page Start: 521
• Page End: 525
• Publication Date: 2015-12-04
• Subjects: cycloaddition -- cyclopropanes -- heterocycles -- Lewis acids; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201504013
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Donor–acceptor cyclopropanes were reacted with amphiphilic benzodithioloimine to give seven‐membered heterocycles with two sulfur atoms. Formally, this transformation can be regarded as a [4+3] cycloaddition reaction of the three‐membered ring and ortho ‐bisthioquinone. The benzodithioloimine serves as a surrogate for this highly reactive diene. The structure of the products was confirmed by X‐ray crystallography. Broad signals in 13 C NMR studies suggest that several conformers, slowly interconverting on the NMR timescale, are present at room temperature. Abstract : Hetero‐[4+3] : Benzodithioloimine bearing two sulfur atoms with strongly amphiphilic character was reacted with donor–acceptor cyclopropanes to give seven‐membered heterocycles in good to excellent yields (see scheme).