An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement

We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 °C in the melt).

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Bibliographic Details
Published in:Organic letters 2005-03, Vol.7 (5), p.783-786
Main Authors: Bendikov, Michael, Duong, Hieu M, Bolanos, Eduardo, Wudl, Fred
Format: Article
Language:English
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Summary:We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 °C in the melt).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0477327