Ozonolysis of a series of 1-substituted indenes. The substituent steric effects on the ozonide exo/endo ratios

Masahiro Miura, Masatomo Nojima, Shigekazu Kusabayashi, Kevin J. McCullough

Research output: Contribution to journalArticle

Abstract

The ozonolysis of a series of disubstituted (1,2 and 1,3) and trisubstituted (1,2,3) indenes 1-28 in carbon tetrachloride at 20°C has been investigated. The major product in each case was the corresponding bicyclic ozonide, usually obtained as a mixture of exo and endo isomers, whose ratio varied markedly, but inconsistently, with the nature of the 1- and 2-substituents. Since the product stereochemistry was found to show little dependence on the relative isomer stability or the substituent electronic effects, the results have been discussed in terms of the direction of approach of the ozone to the indene substrate. © 1984 American Chemical Society.

Original languageEnglish
Pages (from-to)2932-2936
Number of pages5
JournalJournal of the American Chemical Society
Volume106
Issue number10
Publication statusPublished - 1984

Fingerprint

Indenes
Isomers
Stereochemistry
Carbon Tetrachloride
Ozone
Substrates
1,2,4-trioxane

Cite this

Miura, Masahiro ; Nojima, Masatomo ; Kusabayashi, Shigekazu ; McCullough, Kevin J. / Ozonolysis of a series of 1-substituted indenes. The substituent steric effects on the ozonide exo/endo ratios. In: Journal of the American Chemical Society. 1984 ; Vol. 106, No. 10. pp. 2932-2936.
@article{348eda3adc624deabef499efee7b91a2,
title = "Ozonolysis of a series of 1-substituted indenes. The substituent steric effects on the ozonide exo/endo ratios",
abstract = "The ozonolysis of a series of disubstituted (1,2 and 1,3) and trisubstituted (1,2,3) indenes 1-28 in carbon tetrachloride at 20°C has been investigated. The major product in each case was the corresponding bicyclic ozonide, usually obtained as a mixture of exo and endo isomers, whose ratio varied markedly, but inconsistently, with the nature of the 1- and 2-substituents. Since the product stereochemistry was found to show little dependence on the relative isomer stability or the substituent electronic effects, the results have been discussed in terms of the direction of approach of the ozone to the indene substrate. {\circledC} 1984 American Chemical Society.",
author = "Masahiro Miura and Masatomo Nojima and Shigekazu Kusabayashi and McCullough, {Kevin J.}",
year = "1984",
language = "English",
volume = "106",
pages = "2932--2936",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "10",

}

Ozonolysis of a series of 1-substituted indenes. The substituent steric effects on the ozonide exo/endo ratios. / Miura, Masahiro; Nojima, Masatomo; Kusabayashi, Shigekazu; McCullough, Kevin J.

In: Journal of the American Chemical Society, Vol. 106, No. 10, 1984, p. 2932-2936.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Ozonolysis of a series of 1-substituted indenes. The substituent steric effects on the ozonide exo/endo ratios

AU - Miura, Masahiro

AU - Nojima, Masatomo

AU - Kusabayashi, Shigekazu

AU - McCullough, Kevin J.

PY - 1984

Y1 - 1984

N2 - The ozonolysis of a series of disubstituted (1,2 and 1,3) and trisubstituted (1,2,3) indenes 1-28 in carbon tetrachloride at 20°C has been investigated. The major product in each case was the corresponding bicyclic ozonide, usually obtained as a mixture of exo and endo isomers, whose ratio varied markedly, but inconsistently, with the nature of the 1- and 2-substituents. Since the product stereochemistry was found to show little dependence on the relative isomer stability or the substituent electronic effects, the results have been discussed in terms of the direction of approach of the ozone to the indene substrate. © 1984 American Chemical Society.

AB - The ozonolysis of a series of disubstituted (1,2 and 1,3) and trisubstituted (1,2,3) indenes 1-28 in carbon tetrachloride at 20°C has been investigated. The major product in each case was the corresponding bicyclic ozonide, usually obtained as a mixture of exo and endo isomers, whose ratio varied markedly, but inconsistently, with the nature of the 1- and 2-substituents. Since the product stereochemistry was found to show little dependence on the relative isomer stability or the substituent electronic effects, the results have been discussed in terms of the direction of approach of the ozone to the indene substrate. © 1984 American Chemical Society.

UR - http://www.scopus.com/inward/record.url?scp=0021436235&partnerID=8YFLogxK

M3 - Article

VL - 106

SP - 2932

EP - 2936

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 10

ER -