Photochemistry of 9-methylbicyclo[3.3.1]nonyl aryl ketones--a novel 1,5-disproportionation of 1,4-hydroxy biradicals and asymmetric induction using the solid-state ionic chiral auxiliary method (1). Canadian Journal of Chemistry | September 1, 2005| | COPYRIGHT 2005 NRC Research Press. This material is published under license from the publisher through the Gale Group, Farmington Hills, Michigan.  All inquiries regarding rights should be directed to the Gale Group. (Hide copyright information) Copyright

Introduction

Triplet 1,4-hydroxy biradicals formed in the [gamma]-hydrogen abstraction step of the photochemical Norrish-Yang type II reaction have three possible fates: reverse hydrogen transfer to regenerate the starting ketone in its ground state, cleavage of the central carbon-carbon bond to form an alkene and an enol, and Yang cyclization to form a cyclobutanol derivative (Scheme 1) (1). In this paper, we reporta fourth reaction pathway, a novel 1,5-disproportionation, observed for the 1,4-hydroxy biradicals derived from hydrogen abstraction of ...

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