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New synthesis of 1,2-bismethylenecyclobutanes by [2+2] cycloaddition reaction of 1,1-diphenyl-4,4-bis(trifluoromethyl)-butatriene with electron-rich alkenes

✍ Scribed by Hans Gotthardt; Rüdiger Jung

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 119 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81399-x

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✦ Synopsis

The titZe compound 1 undergoes thermal [n2s+a2s] cycZoaddition reactions with l,l-di-methoxyethylene or enamines to produce 1,2-bismethyZenecycZobutanes of type 3. Butatrienes display an interesting position-selectivebehaviortowards cycloaddition reactions. For example, recently it has been established that several substituted butatrienes react with 1,3 dipoles like diazomethane 1 or 1,3-dithiolylium-4-elates 2,3 at one of the terminal double bonds exclusively and not at the central one. In connection with this stud-y, we wish to report preliminary results on [2+2] cycloaddition reactions which position-specifically take place at the central double bond of the title butatriene. To our knowledge there is no report on thermal [2+2] cycloaddition reactions of butatrienes to CC double bonds except photochemical dimerization of tetraarylbutatrienes 4 .

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