Chemical transformations of solvent-derived ozonolysis products: Improved synthesis of polycyclic 1,2,4,6-tetroxepanes from α-alkoxy α′-hydroperoxy cyclic ethers and aldehydes

Kevin J. McCullough; Yoshihiro Ushigoe; Shogo Tanaka; Araki Masuyama; Masatomo Nojima

Chemical transformations of solvent-derived ozonolysis products: Improved synthesis of polycyclic 1,2,4,6-tetroxepanes from α-alkoxy α′-hydroperoxy cyclic ethers and aldehydes

Kevin J. McCullough
, Yoshihiro Ushigoe
, Shogo Tanaka
, Araki Masuyama
, Masatomo Nojima

School of Engineering & Physical Sciences

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

5 Citations (Scopus)

Abstract

a-Alkoxy a'-hydroperoxy cyclic ethers condense with aliphatic aldehydes under acidic conditions to produce the bicyclic 1,2,4,6-tetroxepanes. By X-ray crystallographic analysis, the tetroxepanes 5b and 12b, derived from cyclocondensation of the hydroperoxides 4 and 8 respectively with acetaldehyde, were shown to be exo-isomers.

Original language	English
Pages (from-to)	3053-3057
Number of pages	5
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	18
Publication status	Published - 1998

Cite this

@article{627ddd1d9a4f4ce6a87e3855ab1edb7c,

title = "Chemical transformations of solvent-derived ozonolysis products: Improved synthesis of polycyclic 1,2,4,6-tetroxepanes from α-alkoxy α′-hydroperoxy cyclic ethers and aldehydes",

abstract = "a-Alkoxy a'-hydroperoxy cyclic ethers condense with aliphatic aldehydes under acidic conditions to produce the bicyclic 1,2,4,6-tetroxepanes. By X-ray crystallographic analysis, the tetroxepanes 5b and 12b, derived from cyclocondensation of the hydroperoxides 4 and 8 respectively with acetaldehyde, were shown to be exo-isomers.",

author = "McCullough, \{Kevin J.\} and Yoshihiro Ushigoe and Shogo Tanaka and Araki Masuyama and Masatomo Nojima",

year = "1998",

language = "English",

pages = "3053--3057",

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

issn = "0300-922X",

number = "18",

}

Chemical transformations of solvent-derived ozonolysis products: Improved synthesis of polycyclic 1,2,4,6-tetroxepanes from α-alkoxy α′-hydroperoxy cyclic ethers and aldehydes. / McCullough, Kevin J.; Ushigoe, Yoshihiro; Tanaka, Shogo et al.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 18, 1998, p. 3053-3057.

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

TY - JOUR

T1 - Chemical transformations of solvent-derived ozonolysis products

T2 - Improved synthesis of polycyclic 1,2,4,6-tetroxepanes from α-alkoxy α′-hydroperoxy cyclic ethers and aldehydes

AU - McCullough, Kevin J.

AU - Ushigoe, Yoshihiro

AU - Tanaka, Shogo

AU - Masuyama, Araki

AU - Nojima, Masatomo

PY - 1998

Y1 - 1998

N2 - a-Alkoxy a'-hydroperoxy cyclic ethers condense with aliphatic aldehydes under acidic conditions to produce the bicyclic 1,2,4,6-tetroxepanes. By X-ray crystallographic analysis, the tetroxepanes 5b and 12b, derived from cyclocondensation of the hydroperoxides 4 and 8 respectively with acetaldehyde, were shown to be exo-isomers.

AB - a-Alkoxy a'-hydroperoxy cyclic ethers condense with aliphatic aldehydes under acidic conditions to produce the bicyclic 1,2,4,6-tetroxepanes. By X-ray crystallographic analysis, the tetroxepanes 5b and 12b, derived from cyclocondensation of the hydroperoxides 4 and 8 respectively with acetaldehyde, were shown to be exo-isomers.

UR - https://www.scopus.com/pages/publications/33751303798

M3 - Article

SN - 0300-922X

SP - 3053

EP - 3057

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 18

ER -

Chemical transformations of solvent-derived ozonolysis products: Improved synthesis of polycyclic 1,2,4,6-tetroxepanes from α-alkoxy α′-hydroperoxy cyclic ethers and aldehydes

Abstract

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