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Phillips DL, Fang WH, Zheng X. Isodiiodomethane is the methylene transfer agent in cyclopropanation reactions with olefins using ultraviolet photolysis of diiodomethane in solutions: a density functional theory investigation of the reactions of isodiiodomethane, iodomethyl radical, and iodomethyl cation with ethylene. J Am Chem Soc. 2001;123(18):4197-203doi: 10.1021/ja003090g.
Phillips, D. L., Fang, W. H., & Zheng, X. (2001). Isodiiodomethane is the methylene transfer agent in cyclopropanation reactions with olefins using ultraviolet photolysis of diiodomethane in solutions: a density functional theory investigation of the reactions of isodiiodomethane, iodomethyl radical, and iodomethyl cation with ethylene. Journal of the American Chemical Society, 123(18), 4197-203. https://doi.org/10.1021/ja003090g
Phillips, D L, et al. "Isodiiodomethane is the methylene transfer agent in cyclopropanation reactions with olefins using ultraviolet photolysis of diiodomethane in solutions: a density functional theory investigation of the reactions of isodiiodomethane, iodomethyl radical, and iodomethyl cation with ethylene." Journal of the American Chemical Society vol. 123,18 (2001): 4197-203. doi: https://doi.org/10.1021/ja003090g
Phillips DL, Fang WH, Zheng X. Isodiiodomethane is the methylene transfer agent in cyclopropanation reactions with olefins using ultraviolet photolysis of diiodomethane in solutions: a density functional theory investigation of the reactions of isodiiodomethane, iodomethyl radical, and iodomethyl cation with ethylene. J Am Chem Soc. 2001 May 09;123(18):4197-203. doi: 10.1021/ja003090g. PMID: 11457184.
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J Am Chem Soc. 2001 May 09;123(18):4197-203. doi: 10.1021/ja003090g.

Isodiiodomethane is the methylene transfer agent in cyclopropanation reactions with olefins using ultraviolet photolysis of diiodomethane in solutions: a density functional theory investigation of the reactions of isodiiodomethane, iodomethyl radical, and iodomethyl cation with ethylene.

Journal of the American Chemical Society

D L Phillips, W H Fang, X Zheng

Affiliations

  1. Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong S. A. R., P. R. China.

PMID: 11457184 DOI: 10.1021/ja003090g

Abstract

We examine the chemical reactions of the isodiiodomethane (CH2I-I), .CH2I and CH2I(+) species with ethylene using density functional theory computations. The CH2I-I species readily reacts with ethylene to give the cyclopropane product and an I2 product via a one-step reaction with a barrier height of approximately 2.9 kcal/mol. However, the.CH2I and CH2I(+) species have much more difficult pathways (with larger potential barriers) to react with ethylene via a two-step reaction mechanism. Comparison of experimental results to our present calculation results indicates that the CH2I-I photoproduct species is most likely the methylene transfer agent for the cyclopropanation reaction of olefins via ultraviolet photoexcitation of diiodomethane.

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