Rate and Product Studies of 1-Adamantylmethyl Haloformates Under Solvolytic Conditions
- Title
- Rate and Product Studies of 1-Adamantylmethyl Haloformates Under Solvolytic Conditions
- Author
- 이용우
- Keywords
- 1-Adamantylmethyl haloformates; Grunwald-Winstein equation; Leaving group effect; Solvent isotope effect
- Issue Date
- 2012-11
- Publisher
- 대한화학회
- Citation
- Bulletin of the Korean Chemical Society, v. 33, NO. 11, Page. 3657-3664
- Abstract
- Reactions of 1-adamantylmethyl chloroformate (1-AdCH2OCOCl, 1) and 1-adamantylmethyl fluoroformate (1-AdCH2OCOF, 2) in hydroxylic solvents have been studied. Application of the extended Grunwald-Winstein (G-W) equation to solvolyses of 1 in a variety of pure and binary solvents indicates an addition-elimination pathway in the majority of the solvents except an ionization pathway in the solvents of relatively low nucleophilcity and high ionizing power. The solvolyses of 2 show an addition-elimination pathway in all of the mixed solvents. The leaving group effects (kF/kCl), the kinetic solvent isotope effects (KSIEs, kMeOH/kMeOD), and the enthalpy and entropy of activation for the solvolyses of 1 and 2 were also calculated. The selectivity values (S) for each solvent composition are reported and discussed. These observations are compared with those previously reported for other alkyl haloformate esters.
- URI
- http://koreascience.or.kr/article/JAKO201236135723022.pagehttps://repository.hanyang.ac.kr/handle/20.500.11754/184165
- ISSN
- 0253-2964;1229-5949
- DOI
- 10.5012/bkcs.2012.33.11.3657
- Appears in Collections:
- COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > CHEMICAL AND MOLECULAR ENGINEERING(화학분자공학과) > Articles
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