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An unexpected Diels‐Alder type cycloaddition of cyclic enone ethylene ketals
Author(s) -
Chow Yuan L.,
Cheng XianEn,
Zhang YuHuang
Publication year - 1993
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19930110409
Subject(s) - chemistry , cyclopentenone , cycloaddition , enone , cyclohexenone , diels–alder reaction , acetonitrile , organic chemistry , hydrolysis , stereoselectivity , ethylene , catalysis
The ethylene ketal of 2‐cyclopentenone and 2‐cyclohexenone in acetonitrile in the presence of a trace of an acid rapidly undergoes the Diels‐Alder type dimerization. The products are regiospecific but not stereoselective and are hydrolysed sequentially to afford keto‐ketals and diketones whose structures are determined by extensive applications of NMB spectroscopy.