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;
1997-01-01
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.File in questo prodotto:
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