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| - Intramolecular Reactions of Benzylic Azides with Ketones: Competition between Schmidt and Mannich Pathways
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| Abstract
| - The Lewis acid-promoted reactions of benzylic azides with ketones can proceed by two majorpathways. The azido-Schmidt reaction involves simple addition of azide to the ketone followed byrearrangement and ring expansion. In addition, benzylic azides can undergo prior rearrangementto afford iminium ions that can subsequently participate in a Mannich reaction. A series of ketonescontaining an α CH2(CH2)nCH(N3)Ph substituent (n = 1−3) was prepared to investigate thedependence of products on ketone ring size and tether length. For all ketones examined, good yieldsof bicyclic lactams arising from intramolecular Schmidt reaction were obtained when a four-carbonlinker was used (n = 1 in the above formulation), but Mannich products predominated for thelonger tethers examined (n = 2, 3).
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