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Chemistry of o ‐Benzoquinones and Masked o ‐Benzoquinones. VI. Cycloaddition of 6, 9 Dipropyl‐1, 4‐Dioxaspiro[4.5] Deca‐6, 8‐Dien‐2, 10‐Dione with Cycloheptatriene
Author(s) -
Hsu Y. H.,
Kuo L. C.,
Liao C. C.
Publication year - 1984
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198400027
Subject(s) - chemistry , cycloheptatriene , cycloaddition , dehydrogenation , deca , benzoquinone , medicinal chemistry , adduct , hydrolysis , catechol , organic chemistry , catalysis
Cycloaddition of masked o ‐benzoquinone, 6,9‐dipropyl‐1, 4‐dioxaspiro[4.5]deca‐6, 8‐dien‐2,10‐dione, with cycloheptatriene afforded mainly [4π+2π] adducts which was transformed into 1, 4‐dipropyl‐5H‐benzocycloheptene by hydrolysis, photolysis and dehydrogenation consecutively. These reaction sequences represent a novel method for the synthesis of 5H‐benzocycloheptene from catechol via masked o ‐benzoquinone.