Synthesis and x-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]-undecanes

Masahiro Miura; Akio Ikegami; Masatomo Nojima; Shigekazu Kusabayashi; Kevin J. McCullough; Malcolm D. Walkinshaw

Synthesis and x-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]-undecanes

Masahiro Miura, Akio Ikegami, Masatomo Nojima, Shigekazu Kusabayashi, Kevin J. McCullough, Malcolm D. Walkinshaw

School of Engineering & Physical Sciences

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

9 Citations (Scopus)

Abstract

The reactions of bicyclic ozonides and aldehyde- or ketone-derived peroxides, preformed or generated in situ, in the presence of chlorosulphonic acid afford the corresponding 2,3,5,6,11 -pentaoxabicyclo-[5.3.1] undecanes. In addition, 1,2,4,5-tetraoxans are often isolated from the product mixture. Mechanisms are proposed to account for the observed peroxidic products. An X-ray analysis of the crystalline product (4b) confirms the general structure and reveals that it is solely the exo-isomer.

Original language	English
Pages (from-to)	1657-1664
Number of pages	8
Journal	Journal of the Chemical Society, Perkin Transactions 1
Publication status	Published - 1983

Cite this

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title = "Synthesis and x-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]-undecanes",

abstract = "The reactions of bicyclic ozonides and aldehyde- or ketone-derived peroxides, preformed or generated in situ, in the presence of chlorosulphonic acid afford the corresponding 2,3,5,6,11 -pentaoxabicyclo-[5.3.1] undecanes. In addition, 1,2,4,5-tetraoxans are often isolated from the product mixture. Mechanisms are proposed to account for the observed peroxidic products. An X-ray analysis of the crystalline product (4b) confirms the general structure and reveals that it is solely the exo-isomer.",

author = "Masahiro Miura and Akio Ikegami and Masatomo Nojima and Shigekazu Kusabayashi and McCullough, \{Kevin J.\} and Walkinshaw, \{Malcolm D.\}",

year = "1983",

language = "English",

pages = "1657--1664",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

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TY - JOUR

T1 - Synthesis and x-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]-undecanes

AU - Miura, Masahiro

AU - Ikegami, Akio

AU - Nojima, Masatomo

AU - Kusabayashi, Shigekazu

AU - McCullough, Kevin J.

AU - Walkinshaw, Malcolm D.

PY - 1983

Y1 - 1983

N2 - The reactions of bicyclic ozonides and aldehyde- or ketone-derived peroxides, preformed or generated in situ, in the presence of chlorosulphonic acid afford the corresponding 2,3,5,6,11 -pentaoxabicyclo-[5.3.1] undecanes. In addition, 1,2,4,5-tetraoxans are often isolated from the product mixture. Mechanisms are proposed to account for the observed peroxidic products. An X-ray analysis of the crystalline product (4b) confirms the general structure and reveals that it is solely the exo-isomer.

AB - The reactions of bicyclic ozonides and aldehyde- or ketone-derived peroxides, preformed or generated in situ, in the presence of chlorosulphonic acid afford the corresponding 2,3,5,6,11 -pentaoxabicyclo-[5.3.1] undecanes. In addition, 1,2,4,5-tetraoxans are often isolated from the product mixture. Mechanisms are proposed to account for the observed peroxidic products. An X-ray analysis of the crystalline product (4b) confirms the general structure and reveals that it is solely the exo-isomer.

UR - https://www.scopus.com/pages/publications/37049113049

M3 - Article

SN - 1472-7781

SP - 1657

EP - 1664

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

Synthesis and x-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]-undecanes

Abstract

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