81667-41-6Relevant articles and documents
CROSS AND PARALLEL CYCLISATION-REARRANGEMENT OF FACE PROXIMATE ?-2p-C CATIONS GENERATED IN POLYCYCLIC OLEFINS
Astin, Kenneth B.,Fletcher, Adrian V.,Mackenzie, Kenneth,Miller, Andrew S.,Ratcliffe, Norman M.,at al.
, p. 111 - 124 (2007/10/02)
Partially dechlorinated and other derivatives of the cyclodiene pesticides have been made and their behaviour in strongly acid media investigated with a view to correlating structure with cyclisation geometry.The X-ray crystal structure of one key compound unambiguously indicates that in the absence of the dichloromethano-bridge characteristic of the parent pesticides aldrin and isodrin, cross rather than parallel cyclisation is preferred in strongly acid conditions.Successive thermal rearrangements of 1,2,3,4-tetrachlorocyclopentadiene used here in synthesis of useful model compounds is briefly discussed together with certain other acid catalysed transformations of isodrin and dieldrin analogues.Simple Hueckel MO calculations accord with experimental observation.
