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Ring‐opening reactions of 3‐substituted 1‐azabicyclo[1.1.0]butane with dichlorocarbene
Author(s) -
Mlostoń Grzegorz,
Galindo Alberto,
Bartnik Romuald,
Marchand Alan R.,
Rajagopal D.
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330116
Subject(s) - dichlorocarbene , chemistry , chloroform , butane , potassium hydroxide , ring (chemistry) , tetrazole , medicinal chemistry , organic chemistry , reagent , derivative (finance) , benzene , diene , catalysis , natural rubber , financial economics , economics
Reaction of 3‐ethyl‐1‐azabicyclo[1.1.0]butane ( 1a ) with chloroform‐potassium tert ‐butoxide afforded a ring‐opened product, 1,1‐dichloro‐2‐aza‐4‐ethylpenta‐1,4‐diene ( 4a ), which was characterized via conversion to the corresponding N ‐substituted 5‐chloro‐1,2,3,4‐tetrazole, Sa . Reaction of 3‐phenyl‐1‐azabicyclo‐[1.1.0]butane ( 1b ) with “Seyferth's reagent” (PhHgCCl 2 Br) afforded 1,1‐dichloro‐2‐aza‐4‐phenylpenta‐1,4‐diene ( 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 hydroxide‐TEBA) was studied. At short reaction times (0.5 hour), the major reaction product was 4b . However, at longer reaction times (20–30 hours), two secondary products, 8 and 9 , were formed which resulted via subsequent dichlorocyclopropanation of 4b .