Abstract
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) |
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Pages (from-to) | 1127-1128 |
Number of pages | 2 |
Journal | Synlett |
Issue number | 8 |
State | Published - 2000 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry
Keywords
- Arene complexes
- Metallation
- Organometallic chemistry
- Regioselectivity