Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene)

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

doi:10.1016/S0040-4020(01)90489-2

Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene)

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

School of Engineering & Physical Sciences

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

6 Citations (Scopus)

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 language	English
Pages (from-to)	7625-7634
Number of pages	10
Journal	Tetrahedron
Volume	50
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4020(01)90489-2
Publication status	Published - 1994

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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",

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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.

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

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

M3 - Article

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VL - 50

SP - 7625

EP - 7634

JO - Tetrahedron

JF - Tetrahedron

IS - 25

ER -

Polycyclic ozonides and peroxides derived from hexamethyl(Dewar benzene)

Abstract

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