Reaction of 2,4-Dinitrobenzenesulfenyl Chloride with Quadricyclene

Article abstract of DOI:10.1021/jo00347a018

The treatment of quadricyclene with 2,4-dinitrobenzenesulfenyl chloride has been reinvestigated and chloro adducts 1-A and 2b-A as well as acetates 4a-A, 4b-A, 6, and 7 have been obtained.Establishing 2b-A with endo-chloride led to important conclusion that endo-chloride attack occurs by collapse of ion pair.Monitoring changes in the proportions of acetates, especially with added LiClO4, has allowed conclusions about the degree of development of the carbocation intermediates.These conclusions were proposed on the basis of the previously published ideas of stereocontrol by an ion pair.