A synthetic alternative to the Type II Intramolecular 4+3 Cycloaddition Reaction

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A synthetic alternative to the Type II Intramolecular 4+3 Cycloaddition Reaction. / Grainger, Richard; Owoare, RB; Tisselli, P; Steed, JW.

In: The Journal of Organic Chemistry, Vol. 68, 01.01.2003, p. 7899-7902.

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@article{218959c00c054cb5b780478ddcbb0cb8,
title = "A synthetic alternative to the Type II Intramolecular 4+3 Cycloaddition Reaction",
abstract = "Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.",
author = "Richard Grainger and RB Owoare and P Tisselli and JW Steed",
year = "2003",
month = jan,
day = "1",
doi = "10.1021/jo034356f",
language = "English",
volume = "68",
pages = "7899--7902",
journal = "The Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - A synthetic alternative to the Type II Intramolecular 4+3 Cycloaddition Reaction

AU - Grainger, Richard

AU - Owoare, RB

AU - Tisselli, P

AU - Steed, JW

PY - 2003/1/1

Y1 - 2003/1/1

N2 - Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.

AB - Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.

UR - http://www.scopus.com/inward/record.url?scp=0141765909&partnerID=8YFLogxK

U2 - 10.1021/jo034356f

DO - 10.1021/jo034356f

M3 - Article

C2 - 14510576

VL - 68

SP - 7899

EP - 7902

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

SN - 0022-3263

ER -