Tetrahedron Letters p. 2537 - 2540 (1993)
Update date:2022-08-04
Topics:
Phillips, Eifion D.
Whitham, Gordon H.
Allylic alkyl sulphones CH2:CHC(Me)2SO2R (R=Me, Et, iPr, tBu, CH2SiMe3, CH2CH2SiMe3, and CH2CH(OH)Me underwent 1,3-rearrangement on treatment with benzoyl peroxide in tBuOH. 1,3-Rearrangement did not occur in cases (R=CH2Ph, CH2COMe) where the intermediate sulphonyl radical RSO2· could undergo loss of sulphur dioxide to form a resonance-stabilised alkyl radical. Allylic 4-pentenyl sulphones undergo rearrangement with accompanying cyclisation of the intermediate radical, this process is more efficient if the allylic sulphone bears an electron withdrawing group at the β-position.
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Doi:10.1021/jacs.6b00032
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