Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers

Ji Duck Kim; Gyoonhee Han; Lak Shin Jeong; Hyun Ju Park; Ok Pyo Zee; Young Hoon Jung

doi:10.1016/S0040-4020(02)00413-1

Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers

Ji Duck Kim, Gyoonhee Han, Lak Shin Jeong, Hyun Ju Park, Ok Pyo Zee, Young Hoon Jung

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

39 Citations (Scopus)

Abstract

The stability order of various alkyl, allyl, and benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl, acryl, benzyl, 2° and allyl carbocations in that order.

Original language	English
Pages (from-to)	4395-4402
Number of pages	8
Journal	Tetrahedron
Volume	58
Issue number	22
DOIs	https://doi.org/10.1016/S0040-4020(02)00413-1
Publication status	Published - 2002 May 27

Bibliographical note

Funding Information:
The authors wish to acknowledge the financial support of the Korea Research Foundation made in the program year of 1998.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(02)00413-1

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title = "Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers",

abstract = "The stability order of various alkyl, allyl, and benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl, acryl, benzyl, 2° and allyl carbocations in that order.",

author = "Kim, {Ji Duck} and Gyoonhee Han and Jeong, {Lak Shin} and Park, {Hyun Ju} and Zee, {Ok Pyo} and Jung, {Young Hoon}",

note = "Funding Information: The authors wish to acknowledge the financial support of the Korea Research Foundation made in the program year of 1998. ",

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T1 - Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers

AU - Kim, Ji Duck

AU - Han, Gyoonhee

AU - Jeong, Lak Shin

AU - Park, Hyun Ju

AU - Zee, Ok Pyo

AU - Jung, Young Hoon

N1 - Funding Information: The authors wish to acknowledge the financial support of the Korea Research Foundation made in the program year of 1998.

PY - 2002/5/27

Y1 - 2002/5/27

N2 - The stability order of various alkyl, allyl, and benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl, acryl, benzyl, 2° and allyl carbocations in that order.

AB - The stability order of various alkyl, allyl, and benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl, acryl, benzyl, 2° and allyl carbocations in that order.

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Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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