Synthesis of new alkenyl iodobenzoate derivatives via Kharasch-Sosnovsky reaction using tert-butyl iodo benzoperoxoate and copper (I) iodide

The synthesis of new alkenyl iodobenzoate derivatives as allylic esters was investigated via the reaction of tert -butyl iodobenzoperoxoate with alkenes in the presence of copper salts. The best result was obtained using tert -butyl-iodobenzoperoxoate in the presence of copper (I) iodide (5 mol%) in...

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Published inJournal of chemical sciences (Bangalore, India) Vol. 132; no. 1
Main Authors Samadi, Saadi, Ashouri, Akram, Majidian, Shiva, I Rashid, Hersh
Format Journal Article
LanguageEnglish
Published New Delhi Springer India 01.12.2020
Springer Nature B.V
Subjects
Acetonitrile
Alkenes
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Copper
Derivatives
Esters
Mass spectra
Refluxing
Regular Article
Alkenyl iodobenzoate
Kharasch–Sosnovsky reaction
Butyl iodobenzoperoxoate
Alkenes
copper (I) iodide
Allylic C–H bond oxidation
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Summary:The synthesis of new alkenyl iodobenzoate derivatives as allylic esters was investigated via the reaction of tert -butyl iodobenzoperoxoate with alkenes in the presence of copper salts. The best result was obtained using tert -butyl-iodobenzoperoxoate in the presence of copper (I) iodide (5 mol%) in refluxing acetonitrile with good yield (92%) in 32 h. The structure of peresters and alkenyl iodobenzoate derivatives were characterized on the basis of their FT-IR, 1 HNMR, 13 CNMR, and Mass spectra. Graphic abstract The preparation of new iodo-allylic esters from alkenes in the presence of copper salts in good to excellent yields is reported in this article.
ISSN:0974-3626
0973-7103
DOI:10.1007/s12039-020-01852-8