STUDY OF THE ANOMERIC EFFECT IN 2-SUBSTITUTED 1,3-DITHIANES

DOI: 10.1016/S0040-4020(01)87344-0

Source and publish data:

Tetrahedron p. 1253 - 1264 (1986)

Update date:2022-08-04

Topics:

Authors:

Juaristi, Eusebio

Tapia, Josefina

Mendez, Rodolfo

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Article abstract of DOI:10.1016/S0040-4020(01)87344-0

The conformational analysis of several 2-substituted 1,3-dithianes made possible the evaluation of S-C-Y anomeric interactions, where Y=SCH3,SC6H5,CO2CH3,COC6H5,CO2H and N(CH3)2.The relative magnitude of the effects observed for these groups <ΔG^o_dithiane(Y)-ΔG^o_cyclohexane(Y)> can be explained in terms of the combined influence of dipole/dipole and two-electron stabilizing interactions (stereoelectronic effect).

Full text of DOI:10.1016/S0040-4020(01)87344-0

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