James Costello James.Costello@uwe.ac.uk
Senior Lecturer
Bi(III) Catalysed O-acylative cleavage of 2,5-dimethyltetrahydrofuran: A substrate dependent borderline mechanism
Costello, James F.; Draffin, William N.; Paver, Simon P.
Authors
William N. Draffin
Simon P. Paver
Abstract
The Bi(III) catalysed O-acylative cleavage of cis- and trans-2,5- dimethyltetrahydrofuran 4 with AcCl, BzCl or i-PrCOCl is stereochemically consistent with the operation of a concerted process (AND N), which proceeds via a stabilised carbocation or 'loose' S N2 transition state. However, the O-acylative cleavage of cis-2,5-dimethyltetrahydrofuran 4 with sterically demanding electrophiles such as t-BuCOCl, appears to be stereochemically consistent with the alternative SN1 (DN+AN) pathway. The apparent merging of mechanistic pathways is rationalised by the participation of a strained acyloxy cation. © 2005 Elsevier Ltd. All rights reserved.
Journal Article Type | Article |
---|---|
Publication Date | Jul 11, 2005 |
Journal | Tetrahedron |
Print ISSN | 0040-4020 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 61 |
Issue | 28 |
Pages | 6715-6719 |
DOI | https://doi.org/10.1016/j.tet.2005.05.014 |
Keywords | O-acylative cleavage, dimethyltetrahydrofuran, substrate dependent, borderline mechanism |
Public URL | https://uwe-repository.worktribe.com/output/1048634 |
Publisher URL | http://dx.doi.org/10.1016/j.tet.2005.05.014 |
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