Issue 25, 2011
From the journal:

Dalton Transactions

Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs†

Christoph Kreitner,a   Stephen J. Geier,a   Louisa J. E. Stanlake,a   Christopher B. Caputoa  and  Douglas W. Stephan*a  

* Corresponding authors

a Department of Chemistry, 80 St. George St., University of Toronto, Toronto, Ontario, Canada
E-mail: dstephan@chem.utoronto.ca

Abstract

While B(C6F5)3 forms the adducts (CH2)4CO2B(C6F5)31 and (CHMeCO2)2B(C6F5)37 with δ-valerolactone and lactide, the frustrated Lewis pairs derived from B(C6F5)3 and phosphine or N-bases react with lactone to effect ring opening affording zwitterionic species of the form L(CH2)4CO2B(C6F5)3 (L = tBu3P 2, Cy3P 3, C5H3Me3N 4, PhNMe2 5, C5H6Me4NH 6) while reaction with rac-lactide results in ring contraction to give salts [LH][OCCHMeCO2(CMe)OB(C6F5)3] (L = tBu3P 8, Cy3P 9, C5H3Me2N 10, C5H6Me4NH 11). The mechanistic implications of these reactions are discussed.

Graphical abstract: Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1DT10449G
Article type
Paper
Submitted
17 Mar 2011
Accepted
26 Apr 2011
First published
25 May 2011

Dalton Trans., 2011,40, 6771-6777

Permissions

Request permissions

Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs

C. Kreitner, S. J. Geier, L. J. E. Stanlake, C. B. Caputo and D. W. Stephan, Dalton Trans., 2011, 40, 6771 DOI: 10.1039/C1DT10449G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements