The four-centre reactions of alkanol–alkoxide negative ions with alkyl ethers and orthoacetates. An ion cyclotron resonance study
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 567-571
- https://doi.org/10.1039/p29850000567
Abstract
Alkoxide–alkanol negative ions [R1O– HOR2] react with carbon ethers (e.g., Me3COR3) by the four-centre reactions [R1O– HOR2]+ Me3COR3→[R2O– HOR3]+ Me3COR1, and [R1O– HOR2]+ Me3COR3→[R1O– HOR3]+ Me3COR2. The former reaction predominates when R1 < R2. In the case of di- and tri-ethers, the four-centre reaction can, in principle, compete with the alternative six-centre reaction. For example, for Me2C(OR3)2, [R1O– HOR2]+ Me2C(OR3)2→ Me2CO + R1OR3+[R2R– HOR3]. Evidence is presented which shows that the six-centre reaction does not occur.Keywords
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