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Silyl stabilization of unsymmetrical bisketenes: 3-(Trimethylsilyl) and 3-(triisopropylsilyl)-2-substituted-1,3-butadiene-1,4-diones

✍ Scribed by Annette D. Allen; Ruizhi Ji; Wing-Yan Lai; Jihai Ma; Thomas T. Tidwell

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 1008 KB
Volume: 5
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520050308

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✦ Synopsis

The bisketenes 2-phenyl and 2-methyl-3-(trimethylsilyl)-1,3-butadiene-l,4dione (8 and 10) are calculated on the basis o f additivity of substituent effects to be less stable than the 3-phenyl and 3-methyl-4-(trimethylsilyI)cyclobut-3-ene-l,2-diones (7 and 9) by 1.9 and 2.6 kcal/mol, respectively. In agreement with this prediction, 8 and 10 are formed by photolysis of 7 and 9, respectively, and undergo thermal reversion to their precursors at similar rates. The concentra- tion of 8 in thermal equilibrium with 7 in CDCI,, as

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