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Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene

✍ Scribed by Ian J.S Fairlamb; Julia M Dickinson; Ileana M Cristea


Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
137 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis


7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladiumcatalysed [ π 2a+ π 2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions.


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