Mechanism of the Meyer--Schuster rearrangement
Journal Article
·
· J. Org. Chem.; (United States)
The mechanism of the Meyer-Schuster rearrangement of tertiary arylpropargyl alcohols to ..cap alpha..,..beta..-unsaturated carbonyl compounds is discussed. The data, inverse solvent isotope effects, k/sub H/sub 2/O/, k/sub D/sub 2/O/ = 0.36-0.48, rho vs. sigma/sup +/ = -2.3 at the reaction site and -1.6 at the rearrangement terminus, (k/sub H//k/sub d/)/sub ..cap alpha../ at the rearrangement terminus = 0.92, and relatively large negative ..delta..S/sup 2 +/, all suggest an ion-dipole intermediate undergoing nucleophilic attack by H/sub 2/O as the rate-determining step. The rearrangement of eight triaryl- and diarylpropargyl alcohols is reported.
- Research Organization:
- Coll. of William and Mary, Williamsburg, VA
- OSTI ID:
- 5241328
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 42:21; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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