13C magnetic resonance studies. 131. An examination of β-enolization in an unsaturated [3.2. 1] system: 3, 3-dimethylbicyclo [3.2. 1] oct-6-en-2-one

…, MTM Clements, S Peiris, JB Stothers

Index: Antoniadis, Greg A.; Clements, Michael T. M.; Peiris, Sriyawathie; Stothers, J. B. Canadian Journal of Chemistry, 1987 , vol. 65, p. 1557 - 1562

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Citation Number: 7

Abstract

Under homoenolization conditions (t-BuO-/t-BuOH/185° C), 3, 3-dimethylbicyclo [3.2. 1] oct-6- en-2-one (5) is converted into six products through three reaction pathways. The major product, 3, 3-dimethylbicyclo [3.3. 0] octan-2-one, arises by unidirectional β-enolate rearrangement of 5 to the isomeric unsaturated [3.3. 0] ketones, which (a) undergo efficient reduction to 2, by single electron transfer, and (b) suffer Haller-Bauer cleavage to two ...

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