Reactions of alkynes with iodine and potassium iodide in acetic acid in the presence of nitrates. Simple synthesis of 1-iodo-2-nitroalkenes

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Abstract

Terminal and internal alkynes react with I2 or KI and nitrates in acetic acid under mild conditions to give the corresponding 1-iodo-2-nitroalkenes as the major products. The effect of the reactant nature and reaction conditions on the yield of products was studied. Oxygen was found to play an important role in the formation of the target products. A possible mechanism of the reaction includes a series of redox transformations of I2 or I- and NO- 3 to form INO2 which then adds to alkynes by a radical path. In reactions with potassium iodide, oxygen acts as an additional oxidant which converts NO into active nitrogen dioxide.

Original languageEnglish
Pages (from-to)1264-1272
Number of pages9
JournalRussian Journal of Organic Chemistry
Volume35
Issue number9
Publication statusPublished - Sep 1999

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Alkynes
Acetic Acid
Nitrates
Oxygen
Potassium Iodide
Nitrogen Dioxide
Oxidants
iodine potassium iodide
Oxidation-Reduction

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Reactions of alkynes with iodine and potassium iodide in acetic acid in the presence of nitrates. Simple synthesis of 1-iodo-2-nitroalkenes",
abstract = "Terminal and internal alkynes react with I2 or KI and nitrates in acetic acid under mild conditions to give the corresponding 1-iodo-2-nitroalkenes as the major products. The effect of the reactant nature and reaction conditions on the yield of products was studied. Oxygen was found to play an important role in the formation of the target products. A possible mechanism of the reaction includes a series of redox transformations of I2 or I- and NO- 3 to form INO2 which then adds to alkynes by a radical path. In reactions with potassium iodide, oxygen acts as an additional oxidant which converts NO into active nitrogen dioxide.",
author = "Yusubov, {M. S.} and Perederina, {I. A.} and Miroshnichenko, {Yulia Yurievna} and Filimonov, {V. D.} and Chi, {Ki Whan}",
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T1 - Reactions of alkynes with iodine and potassium iodide in acetic acid in the presence of nitrates. Simple synthesis of 1-iodo-2-nitroalkenes

AU - Yusubov, M. S.

AU - Perederina, I. A.

AU - Miroshnichenko, Yulia Yurievna

AU - Filimonov, V. D.

AU - Chi, Ki Whan

PY - 1999/9

Y1 - 1999/9

N2 - Terminal and internal alkynes react with I2 or KI and nitrates in acetic acid under mild conditions to give the corresponding 1-iodo-2-nitroalkenes as the major products. The effect of the reactant nature and reaction conditions on the yield of products was studied. Oxygen was found to play an important role in the formation of the target products. A possible mechanism of the reaction includes a series of redox transformations of I2 or I- and NO- 3 to form INO2 which then adds to alkynes by a radical path. In reactions with potassium iodide, oxygen acts as an additional oxidant which converts NO into active nitrogen dioxide.

AB - Terminal and internal alkynes react with I2 or KI and nitrates in acetic acid under mild conditions to give the corresponding 1-iodo-2-nitroalkenes as the major products. The effect of the reactant nature and reaction conditions on the yield of products was studied. Oxygen was found to play an important role in the formation of the target products. A possible mechanism of the reaction includes a series of redox transformations of I2 or I- and NO- 3 to form INO2 which then adds to alkynes by a radical path. In reactions with potassium iodide, oxygen acts as an additional oxidant which converts NO into active nitrogen dioxide.

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