Abstract
TiCl(4) and TiBr(4) 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 [TiX(4)OAc](-) is under thermodynamic control, while the stereoselectivity is governed by kinetics.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Acetates / chemistry*
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Cyclopropanes / chemistry*
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Halogens / chemistry*
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Methylation
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Models, Molecular
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Molecular Structure
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Titanium / chemistry*
Substances
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Acetates
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Cyclopropanes
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Halogens
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cyclopropene
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Titanium