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Solvolysis-Decomposition of 2-Adamantyl Chloroformate: Evidence for Two Reaction Pathways

Title
Solvolysis-Decomposition of 2-Adamantyl Chloroformate: Evidence for Two Reaction Pathways
Author
경진범
Issue Date
2003-03
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v. 68, issue. 9, page. 3425-3432
Abstract
Reaction of 2-adamantyl chloroformate under a variety of solvolytic conditions leads to 2-adamantyl chloride accompanied by solvolysis products, some with and some without retention of the CO2 unit. For example, in 100% ethanol, only 4.8% 2-adamantyl chloride is formed with the mixed carbonate (88%) being the dominant product, and in 100% 2,2,2-trifluoroethanol, the products are both formed with loss of CO2, 59% of the chloride and 41% of the ether. With exclusion of the specific rates in 100% and 90% ethanol and methanol, a good Grunwald−Winstein plot against YCl values (solvent ionizing power) is obtained, with a slope of 0.47 ± 0.03. The results are compared with those reported earlier for 1-adamantyl chloroformate and isopropyl chloroformate and mechanistic conclusions are drawn.
URI
https://pubs.acs.org/doi/10.1021/jo0207426https://repository.hanyang.ac.kr/handle/20.500.11754/155523
ISSN
0022-3263
DOI
10.1021/jo0207426
Appears in Collections:
COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > CHEMICAL AND MOLECULAR ENGINEERING(화학분자공학과) > Articles
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