Helvetica chimica acta

From dichlorocyclopropanes to furans and cyclopentadienes via vinylcarbenes

P Müller, N Pautex

Index: Mueller, Paul; Pautex, Nicole Helvetica Chimica Acta, 1988 , vol. 71, p. 1630 - 1637

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Citation Number: 12

Abstract

Abstract Base-induced elimination of dichlorocarbene adducts 2 to 9-alkoxyphen threnes 1 leads to furans 6, presumably via cyclopropenes 3 which undergo rearrangement to vinylcarbenes 4 and C [BOND] H insertion. By the same sequence, the 9-substituted alkylphenanthrene adduct 10 and 14 afford cyclopentadienes 11 and 15. Carbene adducts of simple enol ethers, however, react differently and give preferentially 2-chloroalken-2- ...

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