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

Kaki, R B and Khan, Faiz Ahmed (2015) A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives. Organic and Biomolecular Chemistry, 13. pp. 299-308. ISSN 1477-0520

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Abstract

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.

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IITH Creators:
IITH CreatorsORCiD
Khan, Faiz AhmedUNSPECIFIED
Item Type: Article
Additional Information: KRB thanks UGC for the award of a fellowship
Uncontrolled Keywords: Olefins; Reaction kinetics; Synthesis (chemical)
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Library Staff
Date Deposited: 05 Mar 2015 09:38
Last Modified: 21 Sep 2017 07:15
URI: http://raiith.iith.ac.in/id/eprint/1373
Publisher URL: https://doi.org/10.1039/c4ob01977f
OA policy: http://www.sherpa.ac.uk/romeo/issn/1477-0520/
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