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Efficient preparation and thermal rearrangement of β-(2-vinylcyclopropyl)-α,β-unsaturated ketones. Convenient cycloheptane annelations.

✍ Scribed by Edward Piers; Isao Nagakura

Book ID: 104226158
Publisher: Elsevier Science
Year: 1976
Tongue: French
Weight: 105 KB
Volume: 17
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)93890-5

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✦ Synopsis

The thermal Cope rearrangement of 1,2-divinylcyclopmpane systems to afford the corresponding cycloheptadienes is, particularly if the vinyl substituents are a-oriented, a very facile process which hasbeen the subject of considerable study'. However, this type of conversion has received relatively little application in synthetic organic chemistry. Clearly, the very cornnan occurrence of seven-membered rings in many different classes of natural products provides impetus for investigations regarding the possibility of using this type of transformation in synthesis. Recently, Marina and Kaneko have demonstrated the use of thermal rearrangement of substituted 3-(Z-vinylcyclopropyl)-Z-cyclohexen-l-ones' and 2-methyl-3-(Z-vinylcyclopropyl)-

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