Journal of the Chemical Society. Perkin transactions I p. 1173 - 1178 (1988)
Update date:2022-08-05
Topics:
Crabb, Trevor A.
Trethewey, Andrew N.
Takeuchi, Yoshito
The position of conformational equilibria (CDCl3 solution; 298 K) of perhydrothiazolo<3,4-a>pyridine and the corresponding 6-ethyl-substituted derivatives have been determined by (1)H and (13)C n.m.r. spectroscopy.The reported synthesis of the 1-methylperhydrothiazolo<3,4-a>pyridines via 1-bromo-1-(2-piperidyl)ethane hydrobromide gave in addition the isomeric 9-methylperhydro-3,8-methano-1,3-thiazocines.Contrary to an earlier report trans-(1H,8aH)-1-methylperhydrothiazolo<3,4-a>pyridine was found to adopt an 87percent trans-fused <*> 13percent cis-fused conformational equilibrium (CDCl3; 193 K).
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