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From Dichlorocyclopropanes to Furans and Cyclopentadienes via Vinylcarbenes
Author(s) -
Müller Paul,
Pautex Nicole
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710707
Subject(s) - chemistry , adduct , dichlorocarbene , carbene , enol , base (topology) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
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 CH 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‐ones.