Abstract
The conformation of several 2-(polyhydroxyalkyl)- and 2-(polyacetoxyalkyl)-benzothiazoles has been studied by n.m.r. spectroscopy at 100 MHz in dimethyl sulfoxide- d 6 and chloroform- d solutions, respectively. Compounds having the d- arabino, d- galacto, and d- manno configuration adopt an extended planar conformation in both series. On the other hand, coupling constant data for the d- xylo, d- ribo, and d- gluco configuration indicate that, in these cases, a bent conformation is preferred in which the unfavorable 1,3-dipolar interaction is relieved through rotation at either the C-1-C-2 or C-3-C-4 bond.
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