Perhydroazulenes. 5. Preparation of Perhydroazul-9(10)-en-4-one

Herbert O. House; Joseph H.C. Lee; Don VanDerveer; Jane E. Wissinger

doi:10.1021/jo00174a025

Perhydroazulenes. 5. Preparation of Perhydroazul-9(10)-en-4-one

Herbert O. House, Joseph H.C. Lee, Don VanDerveer, Jane E. Wissinger

Chemistry (Twin Cities)

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

20 Scopus citations

Abstract

An improved procedure for the preparation of perhydroazul-9(10)-en-4-one is described. Crystal structures were determined for two of the reaction intermediates, 1,6-cyclodecanedione and the cyclic diperoxide derived from 1,6-cyclodecanedione. Measurements of ¹³C NMR data at various temperatures were used to determine an activation free energy of 14.8 kcal/mol at 298 K for interconversion of the two chair conformers of the cyclic diperoxide.

Original language	English (US)
Pages (from-to)	5285-5288
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	48
Issue number	26
DOIs	https://doi.org/10.1021/jo00174a025
State	Published - Dec 1983

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abstract = "An improved procedure for the preparation of perhydroazul-9(10)-en-4-one is described. Crystal structures were determined for two of the reaction intermediates, 1,6-cyclodecanedione and the cyclic diperoxide derived from 1,6-cyclodecanedione. Measurements of 13C NMR data at various temperatures were used to determine an activation free energy of 14.8 kcal/mol at 298 K for interconversion of the two chair conformers of the cyclic diperoxide.",

author = "House, {Herbert O.} and Lee, {Joseph H.C.} and Don VanDerveer and Wissinger, {Jane E.}",

year = "1983",

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volume = "48",

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journal = "Journal of Organic Chemistry",

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AU - House, Herbert O.

AU - Lee, Joseph H.C.

AU - VanDerveer, Don

AU - Wissinger, Jane E.

PY - 1983/12

Y1 - 1983/12

N2 - An improved procedure for the preparation of perhydroazul-9(10)-en-4-one is described. Crystal structures were determined for two of the reaction intermediates, 1,6-cyclodecanedione and the cyclic diperoxide derived from 1,6-cyclodecanedione. Measurements of 13C NMR data at various temperatures were used to determine an activation free energy of 14.8 kcal/mol at 298 K for interconversion of the two chair conformers of the cyclic diperoxide.

AB - An improved procedure for the preparation of perhydroazul-9(10)-en-4-one is described. Crystal structures were determined for two of the reaction intermediates, 1,6-cyclodecanedione and the cyclic diperoxide derived from 1,6-cyclodecanedione. Measurements of 13C NMR data at various temperatures were used to determine an activation free energy of 14.8 kcal/mol at 298 K for interconversion of the two chair conformers of the cyclic diperoxide.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Perhydroazulenes. 5. Preparation of Perhydroazul-9(10)-en-4-one

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