Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes

Alexander Tarnovsky; Irmin Pascher; Torbjörn Pascher

doi:10.1021/jp073917u

Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes

Alexander Tarnovsky, Irmin Pascher, Torbjörn Pascher

Chemical Physics

Research output: Contribution to journal › Article › peer-review

Abstract

The metastable CH2I-I and CHI2-I isomers formed by UV photolysis of CH2I2, and CHI3 transfer methylene and iodomethylene groups, respectively, to a variety of cycloalkenes, leading to their cyclopropanation. More than a 100-fold increase of the reaction rate with increasing solvent polarity suggests a dipolar transition state. The fastest second-order rates observed were in CH3CN. However, CH2Cl2 will be the more appropriate reaction medium because the isomer thermal stability is greater in CH2Cl2 than in the more polar CH3CN.

Original language	English
Pages (from-to)	11814-11817
Journal	The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory
Volume	111
Issue number	46
DOIs	https://doi.org/10.1021/jp073917u
Publication status	Published - 2007

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Chemical Physics (S) (011001060)

Subject classification (UKÄ)

Atom and Molecular Physics and Optics

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10.1021/jp073917u

Cite this

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title = "Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes",

abstract = "The metastable CH2I-I and CHI2-I isomers formed by UV photolysis of CH2I2, and CHI3 transfer methylene and iodomethylene groups, respectively, to a variety of cycloalkenes, leading to their cyclopropanation. More than a 100-fold increase of the reaction rate with increasing solvent polarity suggests a dipolar transition state. The fastest second-order rates observed were in CH3CN. However, CH2Cl2 will be the more appropriate reaction medium because the isomer thermal stability is greater in CH2Cl2 than in the more polar CH3CN.",

author = "Alexander Tarnovsky and Irmin Pascher and Torbj{\"o}rn Pascher",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Chemical Physics (S) (011001060)",

year = "2007",

doi = "10.1021/jp073917u",

language = "English",

volume = "111",

pages = "11814--11817",

journal = "The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory",

issn = "1520-5215",

publisher = "The American Chemical Society (ACS)",

number = "46",

}

Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes. / Tarnovsky, Alexander; Pascher, Irmin; Pascher, Torbjörn.
In: The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory, Vol. 111, No. 46, 2007, p. 11814-11817.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes

AU - Tarnovsky, Alexander

AU - Pascher, Irmin

AU - Pascher, Torbjörn

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Chemical Physics (S) (011001060)

PY - 2007

Y1 - 2007

N2 - The metastable CH2I-I and CHI2-I isomers formed by UV photolysis of CH2I2, and CHI3 transfer methylene and iodomethylene groups, respectively, to a variety of cycloalkenes, leading to their cyclopropanation. More than a 100-fold increase of the reaction rate with increasing solvent polarity suggests a dipolar transition state. The fastest second-order rates observed were in CH3CN. However, CH2Cl2 will be the more appropriate reaction medium because the isomer thermal stability is greater in CH2Cl2 than in the more polar CH3CN.

AB - The metastable CH2I-I and CHI2-I isomers formed by UV photolysis of CH2I2, and CHI3 transfer methylene and iodomethylene groups, respectively, to a variety of cycloalkenes, leading to their cyclopropanation. More than a 100-fold increase of the reaction rate with increasing solvent polarity suggests a dipolar transition state. The fastest second-order rates observed were in CH3CN. However, CH2Cl2 will be the more appropriate reaction medium because the isomer thermal stability is greater in CH2Cl2 than in the more polar CH3CN.

U2 - 10.1021/jp073917u

DO - 10.1021/jp073917u

M3 - Article

SN - 1520-5215

VL - 111

SP - 11814

EP - 11817

JO - The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory

JF - The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory

IS - 46

ER -

Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes

Abstract

Bibliographical note

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