Regioselectivity of the insertion reactions of some aromatic diazo compound complexes with cyclomaltoheptaose

Article abstract of DOI:10.1016/0008-6215(92)84039-U

Pyrolysis of solid complexes of aromatic diazo compounds with cyclomaltoheptaose (β-cyclodextrin) yields ether 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.