Smith S H, Forrest S M, Williams D C, Cabell M F, Acquavella M F, Abelt C J
Department of Chemistry, College of William and Mary, Williamsburg, Virginia 23185.
Carbohydr Res. 1992 Jun 16;230(2):289-97. doi: 10.1016/0008-6215(92)84039-u.
Pyrolysis of solid complexes of aromatic diazo compounds with cyclomaltoheptaose (beta-cyclodextrin) yields either derivatives via insertion of carbene into hydroxyl groups. The distribution of the 2-, 3-, and 6-O-isomers indicates that the regioselectivity is moderate. The guest geometry is not as important as its size in determining the ratios of regioisomers. The origins of the regioselectivity are discussed.