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首页> 美国政府科技报告 >Intramolecular (2 + 2) Cycloadditions of Ketenes to Carbonyl Groups. A Novel Synthesis of Substituted Benzofurans
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Intramolecular (2 + 2) Cycloadditions of Ketenes to Carbonyl Groups. A Novel Synthesis of Substituted Benzofurans

机译：Ketenes与羰基的分子内（2 + 2）环加成反应。一种新的取代苯并呋喃的合成

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Intramolecular cycloadditions of ketenes derived from (o-carbonylphenoxy)acetic acids to carbonyl groups have been utilized for the synthesis of substituted benzofurans. Three methods have been employed to generate ketenes in these systems: (i) Method A: base-promoted elimination of hydrogen chloride from (o-carbonylphenoxy)acetyl chlorides; (ii) Method B: reaction of triethylamine with (o-carbonylphenyoxy)acetyl p-tolunesulfonates, (R2CHC(O)OTs), generated in situ via reaction of (o-carbonylphenoxy)acetic acids with p-tolunesulfonyl chloride); (iii) Method C: reaction of triethylamine with esters generated in situ via reaction of (o-carbonylphenoxy)acetic acids with 2-chloro-1-methylphyridinium iodide (Mukaiyama's reagent). Reaction of triethylamine with (2-formylphenoxy)phenylacetyl chloride (Method A), when performed in the presence of excess cyclopentadiene, afforded the corresponding intermolecular (2 + 2) cycloadduct, 7-(2-formylphenoxy)-7-phenylbicyclo(3.2.0)hept-2-en-6-one, thereby providing independent evidence for the fact that a ketene is indeed generated in this reaction.

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