Work

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

Year: 2011

Type: article

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.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c0ob01046d

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

Institutions: California State University, Fullerton, Islamic Azad University, Tehran, University of Tasmania, Islamic Azad University Central Tehran Branch

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, American Chemical Society Petroleum Research Fund, California State University, Fullerton, University of California, Irvine, Australian Research Council, National Institute of General Medical Sciences, Division of Chemistry

Award: Cal State Fullerton MARC U*STAR Program

OpenAlex ID: W2034585671

FWCI: 0.602

Cites: 27

Cited by: 11

Related to: 10