Intramolecular carbene addition to a triple bond - Matrix photochemistry of alpha-diazo-2-ethynylacetophenone

The irradiation (lambda = 403 nm) of alpha-diazo-2-ethynylacetophenone (1a) in solid argon at 10 K leads to (2-ethynylphenyl)ketene (11) as the major product. A minor product is benzo-4-oxo-2,5-cyclohexadienylidene (6) which on 475-nm irradiation reversibly rearranges to cycloprop[a]inden-6(6aH)-one...

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Bibliographic Details
Published inLiebigs Annalen no. 1; pp. 7 - 9
Main Authors Komnick, P, Sander, W
Format Journal Article
LanguageEnglish
Published DEERFIELD BEACH Wiley 01.01.1996
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
carbene addition
REARRANGEMENT
carbene rearrangement
CYCLIZATION REACTION
photochemistry
matrix isolation
ALKYNYL
CYCLOPROPENE
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Summary:The irradiation (lambda = 403 nm) of alpha-diazo-2-ethynylacetophenone (1a) in solid argon at 10 K leads to (2-ethynylphenyl)ketene (11) as the major product. A minor product is benzo-4-oxo-2,5-cyclohexadienylidene (6) which on 475-nm irradiation reversibly rearranges to cycloprop[a]inden-6(6aH)-one (5a). This demonstrates that the intramolecular addition of the carbene center to the double bond can compete with the Wolff rearrangement.
ISSN:0947-3440
DOI:10.1002/jlac.199619960103