Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters.

Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Research Abstract Details 

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Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Abstract Text:

Michael C Pirrung,Tong Ye,Zheng Zhou,John D Simon,

Several mechanistic alternatives proposed for the photochemical deprotection of dimethoxybenzoin esters are presented. Both experimental and theoretical evidence suggest the mechanism is heterolysis of the singlet excited state to form a carboxylate and the alpha-ketocation. The alpha-ketocation has been observed by transient spectroscopy. We propose the alpha-ketocation undergoes electrocyclization to an intermediate with extended conjugation, whose deprotonation gives the observed benzofuran product. A Brønsted study of the rates of benzofuran formation with dimethoxybenzoin esters derived from acids of varying pKa shows the rate is independent of the basicity of the leaving group. In this multistep reaction, benzofuran formation by a final deprotonation is slower than alpha-ketocation generation.

Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Publishing Authors By Initials

MC Pirrung,T Ye,Z Zhou,JD Simon,

For similar investigative techniques: chemistry, analytical: photometry: spectrophotometry research abstracts see: investigative techniques: chemistry, analytical: photometry: spectrophotometry research

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Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Photochemistry and photobiology

VOLUME: 82

Page Numbers: 1258-64

Journal Abbreviation:

ISSN: 0031-8655

DAY: 3

MONTH: 12

YEAR: 2007

Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 376425

Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Keywords Mesh Terms:

KEYWORDS: Spectrophotometry

MESH TERMS: radiation effects

Chemical & Substance for Abstract: Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters. Information

Substance Name: Benzoin

Registry Number: 119-53-9

Grant and Affiliation Information for Mechanistic studies on the photochemical deprotection of 3',5'-dimethoxybenzoin esters.

AFFILIATION: Department of Chemistry, University of California, Riverside, CA 92521-0403 USA. michael.pirrung@ucr.edu

Country: United States

AGENCY: United States NIGMS

GRANT: GM 46720

ACRONYM: GM

MEDLINETA: Photochem Photobiol

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