Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions

Richard N. Butler; Helena A. Gavin; Eamon M. Moloney; Patick McArdle; Desmond Cunningham; Luke A. Burke

doi:10.1016/j.tetlet.2006.06.089

Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions

Richard N. Butler, Helena A. Gavin, Eamon M. Moloney, Patick McArdle, Desmond Cunningham, Luke A. Burke

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

3 Citations (Scopus)

Abstract

The reactions of 1-substituted-imidazolium-3-dicyanomethanides with maleic anhydride gave new ylide products from a Michael reaction and 1,2-rearrangements. These experiments, combined with theoretical calculations, provide an interesting new perspective on the Boekelheide-Fedoruk ring expansions.

Original language	English
Pages (from-to)	6107-6111
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.089
Publication status	Published - 21 Aug 2006
Externally published	Yes

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Butler, R. N., Gavin, H. A., Moloney, E. M., McArdle, P., Cunningham, D., & Burke, L. A. (2006). Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions. Tetrahedron Letters, 47(34), 6107-6111. https://doi.org/10.1016/j.tetlet.2006.06.089

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title = "Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions",

abstract = "The reactions of 1-substituted-imidazolium-3-dicyanomethanides with maleic anhydride gave new ylide products from a Michael reaction and 1,2-rearrangements. These experiments, combined with theoretical calculations, provide an interesting new perspective on the Boekelheide-Fedoruk ring expansions.",

author = "Butler, \{Richard N.\} and Gavin, \{Helena A.\} and Moloney, \{Eamon M.\} and Patick McArdle and Desmond Cunningham and Burke, \{Luke A.\}",

year = "2006",

month = aug,

day = "21",

doi = "10.1016/j.tetlet.2006.06.089",

language = "English",

volume = "47",

pages = "6107--6111",

journal = "Tetrahedron Letters",

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Butler, RN, Gavin, HA, Moloney, EM, McArdle, P, Cunningham, D & Burke, LA 2006, 'Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions', Tetrahedron Letters, vol. 47, no. 34, pp. 6107-6111. https://doi.org/10.1016/j.tetlet.2006.06.089

Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions. / Butler, Richard N.; Gavin, Helena A.; Moloney, Eamon M. et al.
In: Tetrahedron Letters, Vol. 47, No. 34, 21.08.2006, p. 6107-6111.

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

TY - JOUR

T1 - Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride

T2 - new perspectives on the Boekelheide-Fedoruk ring expansions

AU - Butler, Richard N.

AU - Gavin, Helena A.

AU - Moloney, Eamon M.

AU - McArdle, Patick

AU - Cunningham, Desmond

AU - Burke, Luke A.

PY - 2006/8/21

Y1 - 2006/8/21

N2 - The reactions of 1-substituted-imidazolium-3-dicyanomethanides with maleic anhydride gave new ylide products from a Michael reaction and 1,2-rearrangements. These experiments, combined with theoretical calculations, provide an interesting new perspective on the Boekelheide-Fedoruk ring expansions.

AB - The reactions of 1-substituted-imidazolium-3-dicyanomethanides with maleic anhydride gave new ylide products from a Michael reaction and 1,2-rearrangements. These experiments, combined with theoretical calculations, provide an interesting new perspective on the Boekelheide-Fedoruk ring expansions.

UR - https://www.scopus.com/pages/publications/33746337280

U2 - 10.1016/j.tetlet.2006.06.089

DO - 10.1016/j.tetlet.2006.06.089

M3 - Article

SN - 0040-4039

VL - 47

SP - 6107

EP - 6111

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Butler RN, Gavin HA, Moloney EM, McArdle P, Cunningham D, Burke LA. Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions. Tetrahedron Letters. 2006 Aug 21;47(34):6107-6111. doi: 10.1016/j.tetlet.2006.06.089

Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-Fedoruk ring expansions

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