The product distribution obtained in electrophilic reactions of Br 2, N-bromosuccinimmide (NBS), tetrabutylammonium tribromide, tetrabutylammonium bromochloride, NBS-Et3N.3HF, IC1- NaN 3 and MCPBA-KF with tri-O-benzyI-D-glucal in aprotic and protic solvents have been determined by NMR. The results have been rationalized on the basis of the stereoelectronic ct-anomeric effect able to stabilize the transition state related to the electrophilic or nucleophilic step.

Stereoelettronic control in two-step additions to tri-O-benzyl-D-glucal initiated by electrophylic halogens

CHIAPPE, CINZIA;D'ANDREA, FELICIA;
1997

Abstract

The product distribution obtained in electrophilic reactions of Br 2, N-bromosuccinimmide (NBS), tetrabutylammonium tribromide, tetrabutylammonium bromochloride, NBS-Et3N.3HF, IC1- NaN 3 and MCPBA-KF with tri-O-benzyI-D-glucal in aprotic and protic solvents have been determined by NMR. The results have been rationalized on the basis of the stereoelectronic ct-anomeric effect able to stabilize the transition state related to the electrophilic or nucleophilic step.
Bellucci, G; Chiappe, Cinzia; D'Andrea, Felicia; LO MORO, G.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/201705
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