Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes
(2007) In The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory 111(46). p.11814-11817- 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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/971868
- author
- Tarnovsky, Alexander LU ; Pascher, Irmin and Pascher, Torbjörn LU
- organization
- publishing date
- 2007
- type
- Contribution to journal
- publication status
- published
- subject
- in
- The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory
- volume
- 111
- issue
- 46
- pages
- 11814 - 11817
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- wos:000250967800011
- scopus:37049003727
- ISSN
- 1520-5215
- DOI
- 10.1021/jp073917u
- language
- English
- LU publication?
- yes
- additional info
- 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)
- id
- c8cf1c67-545b-47c4-b5a3-e90f3f233fbc (old id 971868)
- date added to LUP
- 2016-04-01 16:47:16
- date last changed
- 2022-02-20 08:31:50
@article{c8cf1c67-545b-47c4-b5a3-e90f3f233fbc, 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 = {{Tarnovsky, Alexander and Pascher, Irmin and Pascher, Torbjörn}}, issn = {{1520-5215}}, language = {{eng}}, number = {{46}}, pages = {{11814--11817}}, publisher = {{The American Chemical Society (ACS)}}, series = {{The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory}}, title = {{Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes}}, url = {{http://dx.doi.org/10.1021/jp073917u}}, doi = {{10.1021/jp073917u}}, volume = {{111}}, year = {{2007}}, }