| Publication Type |
Journal Article |
| Title |
Cleavage of acetylenic substituents from camphor-derivatives by copper(I) chloride |
| Authors |
M Fernanda NN Carvalho Tiago A. Fernandes Ana Sofia Ferreira Luis G. Alves R. Herrmann |
| Groups |
BIOMOL IOARC |
| Journal |
JOURNAL OF ORGANOMETALLIC CHEMISTRY |
| Year |
2008 |
| Month |
August |
| Volume |
693 |
| Number |
17 |
| Pages |
2847-2855 |
| Abstract |
Copper( I) chloride was found to be a highly efficient reagent to promote the cleavage of acetylenic substituents from the camphor skeleton of compounds 1 containing two C - C triple bonds as well as from the compounds 6 and 7 containing one. This is a formal reversal of the formation of these compounds by the reaction of acetylides with keto and imino groups in compound 18. The substituent R at the triple bond modi. es the reactivity and regioselectivity. As intermediates in the process we identi. ed complexes of the types [ Cu( L) depr] ( where ( L) depr denotes a deprotonated camphor- derived ligand ( L)) and [ CuCl( L)]. Quantum mechanical calculations support and rationalize the experimental results. (c) 2008 Elsevier B. V. All rights reserved. |
| DOI |
http://dx.doi.org/10.1016/j.jorganchem.2008.06.004 |
| ISBN |
|
| Publisher |
ELSEVIER SCIENCE SA |
| Book Title |
|
| ISSN |
0022-328X |
| EISSN |
1872-8561 |
| Conference Name |
|
| Bibtex ID |
ISI:000257986500005 |
| Observations |
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