Aryne chemistry. Part XXXV. Reactions of arynes with 1-aminocycloalkenes and hydrolyses of the adducts
Abstract
Reactions of benzyne and tetrahalogenobenzynes with 1-dialkylaminocycloalkenes afford the expected benzocyclobutene derivatives. The hydrolysis of these compounds in the presence of aqueous acid proceeds by C–aryl bond cleavage in the case of the tetrahalogeno-compounds whereas in the hydrolysis of 4b-pyrrolidin-1-yloctahydrobenzo[3,4]cyclobuta[1,2]cyclo-octene, C(4b)–C(10a) bond cleavage is observed