24 0

Rate and Product Studies with 2-Adamantyl Fluoroformate under Solvolytic Conditions

Title
Rate and Product Studies with 2-Adamantyl Fluoroformate under Solvolytic Conditions
Author
경진범
Keywords
2-adamantyl fluoroformate; addition-elimination; Grunwald-Winstein equation; product selectivity
Issue Date
2007-05
Publisher
JOHN WILEY & SONS LTD
Citation
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, v. 20, No. 7, Page. 525-531
Abstract
The specific rates of solvolysis of 2-adamantyl fluoroformate have been measured at 25.0 degrees C in 20 pure and binary solvents. These are well correlated using the extended Grunwald-Winstein equation, with incorporation of the NT solvent nucleophilicity scale and the Y-Cl solvent ionizing power scale. The sensitivities (l = 2.15 +/- 0.17 and m = 0.95 +/- 0.07) toward the changes in solvent nucleophilicity and solvent ionizing power, and the k(F)/k(Cl) values are very similar to those previously observed for solvolyses of n-octyl fluoroformate, consistent with the addition step of an addition-elimination pathway being rate-determining. For aqueous ethanol, measurement of the product ratio allowed selectivity values (S) to be determined. The results are compared with those reported earlier for 2-adamantyl chloroformate and mechanistic conclusions are drawn. Copyright (c) 2007 John Wiley & Sons, Ltd.
URI
https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.1194http://repository.hanyang.ac.kr/handle/20.500.11754/106492
ISSN
0894-3230
DOI
10.1002/poc.1194
Appears in Collections:
ETC > 연구정보
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE