The reactions of 3,7-dimethylenebicyclo[3.3.1]nonane, norbornadiene and cis,cis-1,5-cyclooctadiene with pentafluoro-λ6-sulfanyl chloride

Radical transannular cyclizations of the non-conjugated dienes, such as 3,7-dimethylenebicyclo[3.3.1]nonane and norbornadiene with SF5Cl upon UV-irradiation led to the corresponding SF5-substituted 3,7-noradamantane and nortricyclanes with high yields. Radical reaction of cis,cis-1,5-cyclooctadiene with SF5Cl led to a product of SF5Cl addition to one of the diene double bonds either UV-irradiation or triethylborane were used for radical initiation. (C) 2009 Elsevier B.V. All rights reserved.