Abstract
Gas-phase elimination reactions of deuterium labeled 1-allyl-1-methoxy-6,6-dimethyl-2-cyclohexene (1), 1-methoxy-4,4-dimethyl- 1-vinyl-2-cyclohexene (2) and 3-methoxy-3-methyl-1-butene (3) have been investigated. 1,2-Elimination is the favored pathway when 1 reacts with hydroxide (3.5:1) and methoxide (2.6:1), but 1,4-elimination is preferred with fluoride by 2:1. Abstraction of a vinyl proton in the elimination reactions of 2 and 3 is dominant when amide and/or dimethylamide are used, whereas the loss of an alkyl proton is heavily favored with hydroxide.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 765-768 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 34 |
| Issue number | 5 |
| DOIs | |
| State | Published - Jan 29 1993 |
Keywords
- eliminations
- flowing afterglow
- gas-phase
- methyl ethers
- regiochemistry