Abstract
Reaction of 5-chloromethyl-3-phenyl-4,5-dihydroisoxazole with potassium t-butoxide in dimethyl sulphoxide gives 4-phenyl-2-oxa-3-azabicyclo[3,1,0]hex-3-ene in high yield and reaction of the 5-(1'-chloroethyl) homologue gives high yields of the diastereoisomeric 6-methyl derivatives of the bicyclic system. Some unsuccessful attempts to convert these bicyclic compounds into substituted cyclo-propanols and cyclopropenes are described.
| Original language | English |
|---|---|
| Pages (from-to) | 1855-1858 |
| Number of pages | 4 |
| Journal | Australian Journal of Chemistry |
| Volume | 30 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 1 Jan 1977 |
Cite this
}
Reaction of 5-Chloroalkyl-3-phenyl-4,5-dihydroisoxazoles with strong base. An unexpected new synthesis of the 2-Oxa-3-azabicyclo[3,1,0]hex-3-ene ring system. / George Burrowes, T.; Roy Jackson, W.; Faulks, Suellen; Sharp, Irene.
In: Australian Journal of Chemistry, Vol. 30, No. 8, 01.01.1977, p. 1855-1858.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Reaction of 5-Chloroalkyl-3-phenyl-4,5-dihydroisoxazoles with strong base. An unexpected new synthesis of the 2-Oxa-3-azabicyclo[3,1,0]hex-3-ene ring system
AU - George Burrowes, T.
AU - Roy Jackson, W.
AU - Faulks, Suellen
AU - Sharp, Irene
PY - 1977/1/1
Y1 - 1977/1/1
N2 - Reaction of 5-chloromethyl-3-phenyl-4,5-dihydroisoxazole with potassium t-butoxide in dimethyl sulphoxide gives 4-phenyl-2-oxa-3-azabicyclo[3,1,0]hex-3-ene in high yield and reaction of the 5-(1'-chloroethyl) homologue gives high yields of the diastereoisomeric 6-methyl derivatives of the bicyclic system. Some unsuccessful attempts to convert these bicyclic compounds into substituted cyclo-propanols and cyclopropenes are described.
AB - Reaction of 5-chloromethyl-3-phenyl-4,5-dihydroisoxazole with potassium t-butoxide in dimethyl sulphoxide gives 4-phenyl-2-oxa-3-azabicyclo[3,1,0]hex-3-ene in high yield and reaction of the 5-(1'-chloroethyl) homologue gives high yields of the diastereoisomeric 6-methyl derivatives of the bicyclic system. Some unsuccessful attempts to convert these bicyclic compounds into substituted cyclo-propanols and cyclopropenes are described.
UR - http://www.scopus.com/inward/record.url?scp=0002837424&partnerID=8YFLogxK
U2 - 10.1071/CH9771855
DO - 10.1071/CH9771855
M3 - Article
VL - 30
SP - 1855
EP - 1858
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
SN - 0004-9425
IS - 8
ER -