Addition of Iodonium Nitrate to Unsaturated Hydrocarbons
- 1 February 1971
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 49 (3) , 403-415
- https://doi.org/10.1139/v71-066
Abstract
Iodonium nitrate in chloroform-pyridine at room temperature undergoes a trans stereospecific electrophilic addition to alkenes to form (i) iodoaliphatic nitrate esters, (ii) iodoalkane pyridinium nitrates, or (iii) alkene pyridinium iodides depending on the substrate. The addition is sensitive to steric hindrance effects and anti-Markovnikov addition is commonly encountered. In similar additions to conjugated dienes 1,2-additions in a Markovnikov fashion to form 1:1 adducts of type (ii) are the rule. Terminal acetylenes give alkynyl iodides in fair yield.Keywords
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