Selective functionalization of an isodurene-Cr(CO)(3) complex

Authors
Semmelhack, MF Hilt, G
Citation
Mf. Semmelhack et G. Hilt, Selective functionalization of an isodurene-Cr(CO)(3) complex, SYNLETT, (8), 2000, pp. 1127-1128
Citations number
7
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
8
Year of publication
2000
Pages
1127 - 1128
Database
ISI
SICI code
0936-5214(200008):8<1127:SFOAIC>2.0.ZU;2-1
Abstract
Two synthesis routes to thiol 1 from mesitylene were evaluated. A direct br omination of a 1,2,3,5-tetraalkylbenzene derivative (2) was relatively unse lective and gave the desired bromide in 10% yield. Deprotonation of the cor responding Cr(CO)(3) complex with LiTMP and trapping with a bulky silane (P h(2)tBuSiCl) gave high selectivity for the desired position, apparently thr ough equilibration of benzylic anions and a product-determining trapping st ep.