RING-OPENING REACTIONS OF 3-SUBSTITUTED 1-AZABICYCLO[1.1.0]BUTANE WITH DICHLOROCARBENE

Reaction of 3-ethyl-1-azabicyclo[1.1.0]butane (1a) with chloroform-pot assium tert-butoxide afforded a ring-opened product, 1, 1-dichloro-2-a za-4-ethylpenta-1,4-diene (4a), which was characterized via conversion to the corresponding N-substituted S-chloro-1,2,3,4-tetrazole, 5a. Re action of 3-phenyl-1-azabicyclo[1.1.0]butane (1b) with ''Seyferth's re agent'' (PhHgCCl(2)Br) afforded 1,1-dichloro-2-aza-4-phenylpenta-1,4-d iene (4b), which also was characterized via conversion to a tetrazole derivative, i.e., 5b. Finally, the reaction of 1b with dichlorocarbene generated under phase transfer conditions (chloroform-sodium hydroxid e-TEBA) was studied. At short reaction times (0.5 hour), the major rea ction product was 4b. However, at longer reaction times (20-30 hours), two secondary products, 8 and 9, were formed which resulted via subse quent dichlorocyclopropanation of 4b.