The Journal of Organic Chemistry

Synthesis and stereochemistry of reissert compounds from benzothiazole

A Pandya, HW Gibson

Index: Pandya, Ashish; Gibson, Harry W. Journal of Organic Chemistry, 1993 , vol. 58, # 10 p. 2851 - 2855

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Citation Number: 7

Abstract

Benzothiazole Reissert compounds 1-5 were synthesized, characterized and alkylated to produce 6-9. Conformational analysis of 2 by the use of high resolution (400 MHz) variable temperature NMR spectroscopy indicated that the 2 to E amide conformer ratio is 7921 (* 3%) in CDC13 at 213 K (-60" C) and 57: 43 (* 3%) in C&CD3 at 213 K. Aromatic solvent induced shifts were employed to determine the distribution of rotamers and indicated that ...