Competitive pathways in the dehydrochlorination route to cyclopropa-arenes

Abstract The dehydrochlorination route to cyclopropabenzene 4 from 2 yields t-butoxymethylbenzene 8 as the sole isolable by-product. The path by which the majority of 8 is produced does not involve solvolysis of 4 . The analogous route to cyclopropa[b]naphthalene 3 has been re-examined and the previously proposed 6-chlorobenzo[a]cyclohepta-1,3,5-triene 10 and 2-(t-butoxymethyl)naphthalene 9 have been reassigned as 1-(chloromethyl)naphthalene 5 and 1-(t-butoxymethyl)naphthalene 7 , respectively. Evidence is presented which supports the presence of competing pathways in both dehydrochlorination processes.