[4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone.

Autor: Garve LK; Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.werzlab.de., Pawliczek M; Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.werzlab.de., Wallbaum J; Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.werzlab.de., Jones PG; Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig (Germany)., Werz DB; Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.werzlab.de. d.werz@tu-braunschweig.de.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2016 Jan 11; Vol. 22 (2), pp. 521-5. Date of Electronic Publication: 2015 Dec 04.
DOI: 10.1002/chem.201504013
Abstrakt: 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.
(© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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