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The iodine atom transfer addition reaction (I-ATRA) initiated by AIBN: Optimization, scope and radical reaction pathways

✍ Scribed by Piotr Bałczewski; Aldona Szadowiak; Tomasz Białas

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
206 KB
Volume
17
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Optimization of reaction conditions (alkene, halide, solvent, stoichiometry, manners of the reagents addition, and reaction time) of the I‐ATRA reactions involving 1‐iodoalkylphosphonates was carried out. GC–MS–CI/EI analyses showed main and side products of this reaction and the corresponding radical reaction pathways leading to products derived from phosphorus and nonphosphorus containing iodides, as well as explained the source of hydrogen in radical reduction processes accompanying the I‐ATRA reaction. Synthesis of some 3‐iodoalkyl and 3‐iodoalkenylphosphonates was also presented based on the optimized procedure. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:22–35, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20187

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## Detection of 4-iodo-2,2-dimethyloctanenitrile and 2-iodo-2-methylpropanenitrile proved an operation of two types (I and II) of initiation in the I-ATRA reaction. 4-Iodo-2,2-dimethyloctanenitrile, resulting from the isobutyronitrile radical attack onto 1-hexene followed by the iodine atom transfer