FUNCTIONALIZATION OF THE ALKOXY GROUP OF ALKYL ARYL ETHERS - DEMETHYLATION, ALKYLTHIOLATION AND REDUCTION OF 5-METHOXYINDOLES

Authors
CAUBERE C CAUBERE P RENARD P BIZOTESPIART JG IANELLI S NARDELLI M JAMARTGREGOIRE B
Citation
C. Caubere et al., FUNCTIONALIZATION OF THE ALKOXY GROUP OF ALKYL ARYL ETHERS - DEMETHYLATION, ALKYLTHIOLATION AND REDUCTION OF 5-METHOXYINDOLES, Tetrahedron, 50(47), 1994, pp. 13433-13448
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
47
Year of publication
1994
Pages
13433 - 13448
Database
ISI
SICI code
0040-4020(1994)50:47<13433:FOTAGO>2.0.ZU;2-G
Abstract
In the presence of AlX(3)-RSH three kinds of reactions may take place with 5-methoxy indoles : demethylation, alkylthiolation and reduction. The two latter reactions have never been observed to the present, wit h such reagents. Considerable improvement in the selective demethylati on was found when PhCH(2)SH replaced EtSH previously used in such tran sformations. Factors leading to selective alkylthiolations or reductio ns are shown and mechanisms are proposed to explain these new reaction s.