Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

3-2-2009

Journal or Book Title

The Journal of Organic Chemistry

Volume

74

Issue

7

First Page

2765

Last Page

2770

DOI

10.1021/jo802823s

Abstract

Photolysis of derivatives of dimethylmalonate thiophene-S,C-ylide provides dicarbomethoxycarbene, which can react with thiophene to form dimethyl (2-thienyl)malonate. By generation of dicarbomethoxycarbene from the dibenzothiophene-based ylide in neat thiophene, it is shown that the thienylmalonate is not a product of rearrangement of the thiophene ylide, in contrast to thermolysis results. Formation of the thienylmalonate is suppressed by substitution of any sort in the 2- and 5-positions on the thiophene and by substitution with an electron-withdrawing substituent.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 74(7); 2765-2770. Doi: 10.1021/jo802823s. Copyright 2009 American Chemical Society.

Rights

One-time permission is granted only for the use specified in your request. No additional uses are granted (such as derivative works or other editions). For any other uses, please submit a new request.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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