A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives

An efficient acid induced rearrangement of a tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl system leading to substituted indenones is reported. This domino reaction involves dehydration, olefin isomerization, ketal hydrolysis, [3,3]-sigmatropic rearrangement and dehydrohalogenation. The resultant vi...

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Published inOrganic & biomolecular chemistry Vol. 13; no. 1; pp. 299 - 308
Main Authors Babu, Kaki Raveendra, Khan, Faiz Ahmed
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.01.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TANDEM REACTIONS
REARRANGEMENT
MECHANISM
STRATEGY
CATALYZED ANNULATION
CHEMISTRY
CARBONYLATIVE CYCLIZATION REACTIONS
ALKYNES
EFFICIENT
C-H
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Summary:An efficient acid induced rearrangement of a tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl system leading to substituted indenones is reported. This domino reaction involves dehydration, olefin isomerization, ketal hydrolysis, [3,3]-sigmatropic rearrangement and dehydrohalogenation. The resultant vicinal dihalo olefin moiety in the efficiently generated indenone derivatives was utilized to transform into ninhydrin derivatives by employing Ru(III)-catalyzed oxidation.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01977f