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Generation and cycloadditions of hydroxy(and trimethylsiloxy)phenylethynylketene

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
29
Issue
23
Identifiers
DOI: 10.1016/0040-4039(88)85203-1

Abstract

Abstract An unusual rearrangement of 5,6-dihydroxy-1,3-dimethoxy-5,6-diphenylethynyl-1,3-cyclohexadiene ( 1) to 7-hydroxy-1,4-dimethoxy-2-phenylethynylbicyclo[2.2.2]octadiene-8-one ( 2a) was observed when I was treated with ZnCl 2 in refluxing carbon tetrachloride. The bicyclooctadienones 2a,b were observed to undergo retro Diels-Alder fragmentation at 138 °C to give hydroxy(or trimethylsiloxy)-phenylethynylketenes 3a,b, the only examples of alkynylketenes other than alkynylcyanoketenes to appear in the literature. 1 The ketene 3 b cycloadds to a variety of ketenophiles, but most interestingly, it undergoes unusual reactions with diphenylacetylene to give the cyclopentenedione 7 and with ethoxypropyne to yield the highly functionalized benzocfuinone 8.

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