ABSTRACT: The relative reactivity of a systematic series of simple aliphatic acetate esters has been measured. Exposure of pairs of esters of increasing remote steric hindrance (by altering the degree of branching of the ester alkyl group) to a methanolic solution of Cs2CO3 proved to be a reliable (and general) method for quantitating the rate differences in these base-catalyzed transesterification reactions. The trends in relative rates are in accordance with the qualitative "Rule of Six" put forward by Melvin S. Newman in 1950, as deduced then from interpretation of earlier reports of ease of Fischer esterification reactions.
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Intramolecular Capture of HDDA-Derived Benzynes: (i) 6- to 12-Membered Ring Formation, (ii) Internally (vis-à-vis Remotely) Tethered Traps, and (iii) Role of the Rate of Trapping by the Benzynophile
- Award ID(s):
- 1665389
- PAR ID:
- 10059518
- Date Published:
- Journal Name:
- Organic Letters
- Volume:
- 20
- Issue:
- 1
- ISSN:
- 1523-7060
- Page Range / eLocation ID:
- 88 to 91
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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