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Paper | Special issue | Vol 37, No. 1, 1994, pp.431-439
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S31
Compounds with Bridgehead Nitrogen Part 74. NMR Spectra and Stereochemistry of 1,3,10,10a-Tetrahydro-5H-oxazolo[3,4-b]isoquinoline and 1,5,6,10b-Tetrahydro-3H-oxazolo[4,3-a]isoquinoline

Trevor A. Crabb* and Asmita V. Patel

*Department of Chemistry, University of Potsmouth, Nuffield Centre, St. Michael's Road Portsmouth PO1 2DT, U.K.

Abstract

Whereas 1,3,10,10a-tetrahydro-5H-oxazolo[3,4-b]isoquinoline adopts an equilibrium in CDCl3 solution at 295 K in which the trans-fused conformation predominates, 1,5,6,10b-tetrahydro-3H-oxazolo[4,3-a]isoquinoline adopts the O-inside cis-fused conformation. This difference in conformational preference has been explained partly in terms of ring-fusion strain.