NDLI: Acid generation by 1,4-bis(phenylsulfonyloxy)benzene and their photochemical mechanism

Content Provider	Springer Nature Link
Author	Wu, Ya Wu, Li
Copyright Year	2016
Abstract	Photochemical studies on 1,4-bis(phenylsulfonyloxy)benzene were performed in acetonitrile by steady-state photolysis at 254 nm. Analysis of photoproducts demonstrate that 1,4-bis(phenylsulfonyloxy)benzene undergoes S–O cleavage leading to the formation of phenylsulfonyl radical and phenylsulfonyloxyphenoxy radical which result in the formation of Fries rearrangement products or escape from the solvent cage to undergo further transformations. The involvement of triplet state in the photo-Fries rearrangement was detected. During the irradiation process, a large amount of acidic species were observed and the formation of benzenesulfonic acid was confirmed. Involvement of O2 in the acid generation was proved to be a primary pathway by comparative experiments. Another pathway of acid generation could be explained as a result of disproportionation of sulfonyl radicals due to the formation of thiobenzenesulfonate. The quantification of the acid was determined by the acid–base titration and investigation on steady-state photolysis was carried out by HPLC analysis and GC–MS.
Starting Page	675
Ending Page	682
Page Count	8
File Format	PDF
ISSN	00269247
Journal	Monatshefte für Chemie - Chemical Monthly
Volume Number	148
Issue Number	4
e-ISSN	14344475
Language	English
Publisher	Springer Vienna
Publisher Date	2016-08-22
Publisher Place	Vienna
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Photochemical 1,4-Bis(phenylsulfonyloxy)benzene Photolysis Cage Acid Chemistry/Food Science Organic Chemistry Inorganic Chemistry Analytical Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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