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Regioselectivity of the insertion reactions of some aromatic diazo compound complexes with cyclomaltoheptaose
S H Smith1, S M Forrest, D C Williams
1Department of Chemistry, College of William and Mary, Williamsburg, Virginia 23185.
Carbohydrate Research
|June 26, 1992
Abstract:
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.