Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes

Gary Gallego; Alireza Ariafard; Kiet Tran; David Sandoval; Leera Choi; Yi Hsun Chen; Brian F. Yates; Fu Ming Tao; Christopher J.T. Hyland

doi:10.1039/c0ob01046d

Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes

Gary Gallego, Alireza Ariafard^*, Kiet Tran, David Sandoval, Leera Choi, Yi Hsun Chen, Brian F. Yates, Fu Ming Tao, Christopher J.T. Hyland

^*Corresponding author for this work

Research School of Chemistry

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

10 Citations (Scopus)

Abstract

TiCl₄ and TiBr₄ rapidly transform cyclopropenylmethyl acetates to (E)-halodienes via ring-opening to allyl-vinyl cations. DFT calculations suggest that the regioselectivity of the halogenation of this cationic intermediate by [TiX₄OAc]^- is under thermodynamic control, while the stereoselectivity is governed by kinetics.

Original language	English
Pages (from-to)	3359-3363
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	9
DOIs	https://doi.org/10.1039/c0ob01046d
Publication status	Published - 7 May 2011

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title = "Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes",

abstract = "TiCl4 and TiBr4 rapidly transform cyclopropenylmethyl acetates to (E)-halodienes via ring-opening to allyl-vinyl cations. DFT calculations suggest that the regioselectivity of the halogenation of this cationic intermediate by [TiX4OAc]- is under thermodynamic control, while the stereoselectivity is governed by kinetics.",

author = "Gary Gallego and Alireza Ariafard and Kiet Tran and David Sandoval and Leera Choi and Chen, {Yi Hsun} and Yates, {Brian F.} and Tao, {Fu Ming} and Hyland, {Christopher J.T.}",

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T1 - Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes

AU - Gallego, Gary

AU - Ariafard, Alireza

AU - Tran, Kiet

AU - Sandoval, David

AU - Choi, Leera

AU - Chen, Yi Hsun

AU - Yates, Brian F.

AU - Tao, Fu Ming

AU - Hyland, Christopher J.T.

PY - 2011/5/7

Y1 - 2011/5/7

N2 - TiCl4 and TiBr4 rapidly transform cyclopropenylmethyl acetates to (E)-halodienes via ring-opening to allyl-vinyl cations. DFT calculations suggest that the regioselectivity of the halogenation of this cationic intermediate by [TiX4OAc]- is under thermodynamic control, while the stereoselectivity is governed by kinetics.

AB - TiCl4 and TiBr4 rapidly transform cyclopropenylmethyl acetates to (E)-halodienes via ring-opening to allyl-vinyl cations. DFT calculations suggest that the regioselectivity of the halogenation of this cationic intermediate by [TiX4OAc]- is under thermodynamic control, while the stereoselectivity is governed by kinetics.

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U2 - 10.1039/c0ob01046d

DO - 10.1039/c0ob01046d

M3 - Article

C2 - 21409263

AN - SCOPUS:79954428337

SN - 1477-0520

VL - 9

SP - 3359

EP - 3363

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 9

ER -

Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes

Abstract

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