Tetrahedron p. 5979 - 5986 (1989)
Update date:2022-08-05
Topics:
Ali, Sk. Asrof
Khan, Javaid H.
Wazeer, Mohammed I. M.
Perzanowski, Herman P.
A comparative study of the stereochemical behaviour of the 1,3-dipolar cycloaddition of a series of 1,2-disubstituted alkenes with 1-pyrroline 1-oxide (1) and 2,3,4,5-tetrahydropyridine 1-oxide (2) has been carried out.Both the nitrones exhibit very similar stereochemical properties.Rate constants for the cycloaddition of these nitrones to several disubstituted alkenes have been determined at 36 C by 1H n.m.r. spectroscopy.It is found that the nitrone 1 reacts slower than 2 due to the presence of bond eclipsing strain in the transition state involving 1.
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