Base induced rearrangements of α-halosulfones α-sulfonyl carbanions with bridgehead electrofugal centre |
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| Authors: | J Kattenberg ER De Waard HO Huisman |
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| Institution: | Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, Amsterdam, The Netherlands |
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| Abstract: | The KOtBu-induced Ramberg-Bäcklund reaction of the trans bicyclic halosulfones 1 and 2 is studied in DME and DMSO. Strong indications are obtained that the reaction proceeds via the intermediate Z-episulfone with retention-inversion (involving exo-S-geometry).1 Base induced epimerization at the nucleofugal centre (from axial to equatorial halogen) is demonstrated in DMSO. |
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| Keywords: | Address correspondence to this author |
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