Two synthesis routes to thiol 1 from mesitylene were evaluated. A direct bromination of a 1,2,3,5-tetraalkylbenzene derivative (2) was relatively unselective and gave the desired bromide in 10% yield. Deprotonation of the corresponding Cr(CO)3 complex with LiTMP and trapping with a bulky silane (Ph2tBuSiCl) gave high selectivity for the desired position, apparently through equilibration of benzylic anions and a product-determining trapping step.
|Original language||English (US)|
|Number of pages||2|
|State||Published - Sep 4 2000|
All Science Journal Classification (ASJC) codes
- Organic Chemistry
- Arene complexes
- Organometallic chemistry