Journal of the Chemical Society - Faraday Transactions p. 3237 - 3241 (1990)
Update date:2022-08-16
Topics:
Hindson, Andrew C.
Walton, John C.
The EPR spectra of cycloheptylmethyl, cyclohept-4-enylmethyl and 1,3-dioxacyclohept-5-enylmethyl radicals have been observed.The cycloheptylmethyl radical spectrum shows only a single, average conformation, but for the cycloheptene and dioxacycloheptene rings the CH2* group proved to be a useful probe of the conformations.The preferred conformation of the 1,3-dioxacycloheptene ring was found to depend on the type of substitution at C(2).For the 2-CH2* radical, twist-boat and chair conformers were observed with an Arrhenius activation barrier to inversion of 5 kcal mol-1.For the 2-CH3, 2-CH2* radical the main conformation was the twist-boat.For the 2-Ph, 2CH2* radical the main conformation was the chair; the rotation of the CH2* group was found to be restricted by a barrier of ca. 7.5 kcal mol-1, probably because of steric interaction from two syn axial hydrogens on C(4) and C(7).
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