Acyclic O- and N-substituted pentadienyl cations: Structural characterisation, cyclisation and computational results

James A.S. Howell; Paula J. O'Leary; Paul C. Yates; Zeev Goldschmidt; Hugo E. Gottlieb; Daphna Hezroni-Langerman

doi:10.1016/0040-4020(95)00369-j

Acyclic O- and N-substituted pentadienyl cations: Structural characterisation, cyclisation and computational results

James A.S. Howell
, Paula J. O'Leary
, Paul C. Yates
, Zeev Goldschmidt
, Hugo E. Gottlieb
, Daphna Hezroni-Langerman

Department of Chemistry

Chemistry Department
Keele University
Department of Chemistry
Bar-Ilan University

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

14 Scopus citations

Abstract

A number of 1- and 3-hydroxy and 1-amino substituted acyclic pentadienyl cations have been characterised by NMR spectroscopy in situ at low temperature. Some of the 3-hydroxy cations undergo cyclisation to give 1-hydroxycyclopentenyl cations which on deprotonation give substituted cyclopentenones.

Original language	English
Pages (from-to)	7231-7246
Number of pages	16
Journal	Tetrahedron
Volume	51
Issue number	26
DOIs	https://doi.org/10.1016/0040-4020(95)00369-j
State	Published - 26 Jun 1995

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abstract = "A number of 1- and 3-hydroxy and 1-amino substituted acyclic pentadienyl cations have been characterised by NMR spectroscopy in situ at low temperature. Some of the 3-hydroxy cations undergo cyclisation to give 1-hydroxycyclopentenyl cations which on deprotonation give substituted cyclopentenones.",

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AU - Howell, James A.S.

AU - O'Leary, Paula J.

AU - Yates, Paul C.

AU - Goldschmidt, Zeev

AU - Gottlieb, Hugo E.

AU - Hezroni-Langerman, Daphna

PY - 1995/6/26

Y1 - 1995/6/26

N2 - A number of 1- and 3-hydroxy and 1-amino substituted acyclic pentadienyl cations have been characterised by NMR spectroscopy in situ at low temperature. Some of the 3-hydroxy cations undergo cyclisation to give 1-hydroxycyclopentenyl cations which on deprotonation give substituted cyclopentenones.

AB - A number of 1- and 3-hydroxy and 1-amino substituted acyclic pentadienyl cations have been characterised by NMR spectroscopy in situ at low temperature. Some of the 3-hydroxy cations undergo cyclisation to give 1-hydroxycyclopentenyl cations which on deprotonation give substituted cyclopentenones.

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Acyclic O- and N-substituted pentadienyl cations: Structural characterisation, cyclisation and computational results

Abstract

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