An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies

An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies

Trapping of a pyrimidinone-derived o-quinodimethane with tetraphenylcyclopentadienone gives a mixture of the [4 + 2] and formal [4 + 4] adducts. Computational studies show that the latter arises by a sequence of [4 + 2] cycloaddition, homolysis, radical recombination to a spiro-tetrahydrofuran and C...

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Main Authors: Mohamed Husaini Abdul Rahman, Ramabhadran, Raghunath O., Collier, Steven J., Storr, Richard C., Bates, Roderick Wayland
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2019
Subjects:
Claisen Rearrangement
Cycloaddition
DRNTU::Science::Chemistry
Online Access:https://hdl.handle.net/10356/90300
http://hdl.handle.net/10220/48476
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-903002023-02-28T19:37:06Z An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies Mohamed Husaini Abdul Rahman Ramabhadran, Raghunath O. Collier, Steven J. Storr, Richard C. Bates, Roderick Wayland School of Physical and Mathematical Sciences Claisen Rearrangement Cycloaddition DRNTU::Science::Chemistry Trapping of a pyrimidinone-derived o-quinodimethane with tetraphenylcyclopentadienone gives a mixture of the [4 + 2] and formal [4 + 4] adducts. Computational studies show that the latter arises by a sequence of [4 + 2] cycloaddition, homolysis, radical recombination to a spiro-tetrahydrofuran and Claisen rearrangement under the thermolytic conditions. Accepted version 2019-05-30T02:04:46Z 2019-12-06T17:45:12Z 2019-05-30T02:04:46Z 2019-12-06T17:45:12Z 2017 Journal Article Ramabhadran, R. O., Mohamed Husaini Abdul Rahman, Collier, S. J., Storr, R. C., & Bates, R. W. (2018). An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies. Tetrahedron, 74(1), 1-5. doi:10.1016/j.tet.2017.10.076 0040-4020 https://hdl.handle.net/10356/90300 http://hdl.handle.net/10220/48476 10.1016/j.tet.2017.10.076 en Tetrahedron © 2017 Elsevier Ltd. All rights reserved. This paper was published in Tetrahedron and is made available with permission of Elsevier Ltd. 6 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Claisen Rearrangement
Cycloaddition
DRNTU::Science::Chemistry
spellingShingle Claisen Rearrangement
Cycloaddition
DRNTU::Science::Chemistry
Mohamed Husaini Abdul Rahman
Ramabhadran, Raghunath O.
Collier, Steven J.
Storr, Richard C.
Bates, Roderick Wayland
An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies
description Trapping of a pyrimidinone-derived o-quinodimethane with tetraphenylcyclopentadienone gives a mixture of the [4 + 2] and formal [4 + 4] adducts. Computational studies show that the latter arises by a sequence of [4 + 2] cycloaddition, homolysis, radical recombination to a spiro-tetrahydrofuran and Claisen rearrangement under the thermolytic conditions.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Mohamed Husaini Abdul Rahman
Ramabhadran, Raghunath O.
Collier, Steven J.
Storr, Richard C.
Bates, Roderick Wayland
format Article
author Mohamed Husaini Abdul Rahman
Ramabhadran, Raghunath O.
Collier, Steven J.
Storr, Richard C.
Bates, Roderick Wayland
author_sort Mohamed Husaini Abdul Rahman
title An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies
title_short An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies
title_full An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies
title_fullStr An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies
title_full_unstemmed An unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies
title_sort unusual [4 + 4] cycloadduct from an o-quinodimethane : characterisation and computational studies
publishDate 2019
url https://hdl.handle.net/10356/90300
http://hdl.handle.net/10220/48476
_version_ 1759858099452116992

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