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

Raghunath O. Ramabhadran; Mohamed Husaini bin Abdul Rahman; Steven J. Collier; Richard C. Storr; Roderick W. Bates

doi:10.1016/j.tet.2017.10.076

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

Raghunath O. Ramabhadran^*, Mohamed Husaini bin Abdul Rahman, Steven J. Collier, Richard C. Storr, Roderick W. Bates

^*Corresponding author for this work

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

1 Citation (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1-5
Number of pages	5
Journal	Tetrahedron
Volume	74
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2017.10.076
Publication status	Published - Jan 4 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Ltd

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Claisen rearrangement
Cycloaddition
o-quinodimethane

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10.1016/j.tet.2017.10.076

Cite this

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abstract = "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.",

keywords = "Claisen rearrangement, Cycloaddition, o-quinodimethane",

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AU - Collier, Steven J.

AU - Storr, Richard C.

AU - Bates, Roderick W.

PY - 2018/1/4

Y1 - 2018/1/4

N2 - 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.

AB - 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.

KW - Claisen rearrangement

KW - Cycloaddition

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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