Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene)

Kevin J. McCullough, Shogo Tanaka, Koichi Teshima, Masatomo Nojima

Research output: Contribution to journalArticle

Abstract

A stable, crystalline diozonide, derived from Hexamethyl(Dewar benzene) 1, has been shown by X-ray crystallographic analysis to be the endo,endo-isomer 3c which had been predicted to be less stable than the endo,exo-isomer 3b. Acidolysis of the trans-ozonide 5 in CF3CO2H/CH2Cl2 gave a stable crystalline tricyclic peroxide 6 whereas the isomeric cis-ozonide 7 decomposed under similar conditions.

Original languageEnglish
Pages (from-to)7625-7634
Number of pages10
JournalTetrahedron
Volume50
Issue number25
DOIs
Publication statusPublished - 1994

Fingerprint

Dewars
Peroxides
Benzene
Isomers
Crystalline materials
X rays
1,2,4-trioxane

Cite this

McCullough, K. J., Tanaka, S., Teshima, K., & Nojima, M. (1994). Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene). Tetrahedron, 50(25), 7625-7634. https://doi.org/10.1016/S0040-4020(01)90489-2
McCullough, Kevin J. ; Tanaka, Shogo ; Teshima, Koichi ; Nojima, Masatomo. / Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene). In: Tetrahedron. 1994 ; Vol. 50, No. 25. pp. 7625-7634.
@article{305585d0197d471f9d890fb20be299ed,
title = "Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene)",
abstract = "A stable, crystalline diozonide, derived from Hexamethyl(Dewar benzene) 1, has been shown by X-ray crystallographic analysis to be the endo,endo-isomer 3c which had been predicted to be less stable than the endo,exo-isomer 3b. Acidolysis of the trans-ozonide 5 in CF3CO2H/CH2Cl2 gave a stable crystalline tricyclic peroxide 6 whereas the isomeric cis-ozonide 7 decomposed under similar conditions.",
author = "McCullough, {Kevin J.} and Shogo Tanaka and Koichi Teshima and Masatomo Nojima",
year = "1994",
doi = "10.1016/S0040-4020(01)90489-2",
language = "English",
volume = "50",
pages = "7625--7634",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "25",

}

McCullough, KJ, Tanaka, S, Teshima, K & Nojima, M 1994, 'Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene)', Tetrahedron, vol. 50, no. 25, pp. 7625-7634. https://doi.org/10.1016/S0040-4020(01)90489-2

Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene). / McCullough, Kevin J.; Tanaka, Shogo; Teshima, Koichi; Nojima, Masatomo.

In: Tetrahedron, Vol. 50, No. 25, 1994, p. 7625-7634.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene)

AU - McCullough, Kevin J.

AU - Tanaka, Shogo

AU - Teshima, Koichi

AU - Nojima, Masatomo

PY - 1994

Y1 - 1994

N2 - A stable, crystalline diozonide, derived from Hexamethyl(Dewar benzene) 1, has been shown by X-ray crystallographic analysis to be the endo,endo-isomer 3c which had been predicted to be less stable than the endo,exo-isomer 3b. Acidolysis of the trans-ozonide 5 in CF3CO2H/CH2Cl2 gave a stable crystalline tricyclic peroxide 6 whereas the isomeric cis-ozonide 7 decomposed under similar conditions.

AB - A stable, crystalline diozonide, derived from Hexamethyl(Dewar benzene) 1, has been shown by X-ray crystallographic analysis to be the endo,endo-isomer 3c which had been predicted to be less stable than the endo,exo-isomer 3b. Acidolysis of the trans-ozonide 5 in CF3CO2H/CH2Cl2 gave a stable crystalline tricyclic peroxide 6 whereas the isomeric cis-ozonide 7 decomposed under similar conditions.

UR - http://www.scopus.com/inward/record.url?scp=0028360466&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)90489-2

DO - 10.1016/S0040-4020(01)90489-2

M3 - Article

VL - 50

SP - 7625

EP - 7634

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 25

ER -