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Photochemical Synthesis of 2‐Alkylidene‐1,3‐cyclocalkanediones. Preliminary Communication
Author(s) -
Hobel Klaus,
Margaretha Paul
Publication year - 1987
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19870700410
Subject(s) - chemistry , homolysis , ketene , photodissociation , yield (engineering) , lactone , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , radical , metallurgy , materials science
Abstract Photolysis (λ = 254 nm) of 4‐( tert ‐butyl)‐4,6,7,8‐tetrahydro‐7,7‐dimethy‐2 H ‐1‐benzopyran‐2,5(3 H )‐dione ( 3a ) in t ‐BuOH affords 2‐(2,2‐dimethylpropylidene)‐5,5‐dimethyl‐1,3‐cyclohexanedione ( 1a ) in 80% yield via homolysis of the lactone OCO bond and subsequent ketene elimination.