Regioselectivity of the insertion reactions of some aromatic diazo compound complexes with cyclomaltoheptaose.
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.
Smith
S H
SH
Department of Chemistry, College of William and Mary, Williamsburg, Virginia 23185.
Forrest
S M
SM
Williams
D C
DC
Cabell
M F
MF
Acquavella
M F
MF
Abelt
C J
CJ
D002236:Carbohydrate Conformation; D003505:Cyclodextrins / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D003979:Diazonium Compounds; D007202:Indicators and Reagents; D047392:beta-Cyclodextrins; C031215:betadex