The relative reactivities of ‘normal’ and angle strained cyclo-olefins in 1,3-dipolar cycloaddition reactions. Rotational barriers in nitrones
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 1728-1733
- https://doi.org/10.1039/j29710001728
Abstract
Rate constants for addition of C-phenyl N-methyl nitrone, the ethylcyclohexyl nitrone (II), and dihydroisoquinoline N-oxide respectively to cyclohexene, norbornene, trans-cyclo-octene, and bicyclo[4,2,0]oct-7-ene have been determined. The barrier (ΔG‡) to rotation about the formal double bond in the methylene nitrone (II) is estimated to be ca. 23 kcal mol–1. It is concluded that the low reactivity of C-phenyl N-methyl nitrone and analogous ‘class II’ dipoles towards norbornene is due to steric factors.Keywords
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