@article {1075, title = {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}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {83}, number = {9}, year = {2005}, note = {ISI Document Delivery No.: 001VETimes Cited: 4Cited Reference Count: 29}, month = {Sep}, pages = {1460-1472}, type = {Article}, abstract = {A novel 1.5-disproportionation reaction has been discovered for 1,4-hydroxy biradicals derived from the photolysis of 9-methylbicyclo[3.3.1]nonyl phenyl ketones (1), which undergo mainly Yang cyclization both in Solution and the solid state. By applying the solid-state ionic chiral auxiliary method of asymmetric synthesis to the Yang cyclization, enantiomeric excesses as high as 95\% were achieved at high reaction conversions. The origin of the reaction selectivity is discussed with the help of X-ray crystallography. In addition, the solid-state photoreaction of ketone 1b was found to occur in a single crystal-to-single crystal fashion.}, keywords = {1, 4-hydroxy biradical, asymmetric, BEHAVIOR, CRYSTAL-STRUCTURE, disproportionation, HYDROGEN-BOND, INDUCTION, ionic chiral auxiliary, PHOTOCHEMISTRY, PHOTOCYCLIZATION, reaction, REACTIVITY CORRELATIONS, SALTS, single crystal-to-single crystal}, isbn = {0008-4042}, url = {://000234570000030}, author = {Chen, S. and Patrick, B. O. and Scheffer, J. R.} }