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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
Author(s) -
Shimo Tetsuro,
Minamishin Hidemi,
Somekawa Kenichi
Publication year - 1997
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.5570340230
Subject(s) - chemistry , ring (chemistry) , transformation (genetics) , bicyclic molecule , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , gene
Dehydrochlorination of chlorinated 5‐hydroxy‐2‐oxabicyclo[3.2.0]heptan‐4‐ones, 3a‐c, which were obtained from the photo[2+2]cycloadditions between 4‐hydroxy‐3(2 H )‐furanone 1 and chloroethylenes, with triethylamine gave 2‐ethenyl‐3(2 H )‐furanones 4a,b or 2‐(2‐cyanoethyl)‐3(2 H )‐furanone 4c. 2‐Oxa‐bicyclo[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 by electrocyclic rearrangement.