Reversal of Regioselectivity during Photodimerization of 2-Anthracenecarboxylic Acid in a Water-Soluble Organic Cavitand

Xueqin Wei; A. Mohan Raj; Jiecheng Ji; Wanhua Wu; Giri Babu Veerakanellore; Cheng Yang; Vaidhyanathan Ramamurthy

doi:10.1021/acs.orglett.9b02860

Reversal of Regioselectivity during Photodimerization of 2-Anthracenecarboxylic Acid in a Water-Soluble Organic Cavitand

Xueqin Wei, A. Mohan Raj, Jiecheng Ji, Wanhua Wu, Giri Babu Veerakanellore, Cheng Yang, Vaidhyanathan Ramamurthy

Chemistry

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

The value of octa acid (OA) as a reaction vessel in steering a photoreaction toward a less favored product was established. Photodimerization of 2-anthracenecarboxylic acid within OA yields exclusively head-to-head dimers, while in media such as solution, cyclodextrins (CD) and related hosts yield predominantly head-to-tail dimers. Further, OA enhances the chiral selectivity on the product dimers. The difference between OA and CD is attributed to the variation in the dimensions of their entry ports.

Original language	English (US)
Pages (from-to)	7868-7872
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.9b02860
State	Published - Oct 4 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Reversal of Regioselectivity during Photodimerization of 2-Anthracenecarboxylic Acid in a Water-Soluble Organic Cavitand. / Wei, Xueqin; Raj, A. Mohan; Ji, Jiecheng; Wu, Wanhua; Veerakanellore, Giri Babu; Yang, Cheng; Ramamurthy, Vaidhyanathan.

In: Organic letters, Vol. 21, No. 19, 04.10.2019, p. 7868-7872.

Research output: Contribution to journal › Article › peer-review

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