RING-TRANSFORMATION REACTIONS OF 5-HYDROXY-2-OXABICYCLO[3.2.0]-HEPTAN-4-ONES AND 5-HYDROXY-2-OXABICYCLO[3.2.0]HEPT-6-EN-4-ONES

Authors
SHIMO T MINAMISHIN H SOMEKAWA K
Citation
T. Shimo et al., RING-TRANSFORMATION REACTIONS OF 5-HYDROXY-2-OXABICYCLO[3.2.0]-HEPTAN-4-ONES AND 5-HYDROXY-2-OXABICYCLO[3.2.0]HEPT-6-EN-4-ONES, Journal of heterocyclic chemistry, 34(2), 1997, pp. 533-536
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
34
Issue
2
Year of publication
1997
Pages
533 - 536
Database
ISI
SICI code
0022-152X(1997)34:2<533:RRO5>2.0.ZU;2-W
Abstract
Dehydrochlorination of chlorinated 5-hydroxy-2-oxabicyclo[3.2.0]heptan -4-ones, 3a-c, which were obtained from the photo[2+2]cycloadditions b etween 4-hydroxy-3(2H)-furanone 1 and chloroethylenes, with triethylam ine gave 2-ethenyl-3(2H)-furanones 4a,b or 2-(2-cyanoethyl)-3(2H)-fura none 4c. 2-Oxabicyclo[3.2.0]hept-6-en-4-ones 7 being [2+2]cycloadducts between 1 and acetylenes gave 2,3-dihydro-3-oxooxepin derivatives 8 b y electrocyclic rearrangement.