Aminooxygenation of Ynamides with N-Hydroxybenzotriazoles: Synthesis of α-Benzotriazolyl Carbonyl Compounds
- Title
- Aminooxygenation of Ynamides with N-Hydroxybenzotriazoles: Synthesis of α-Benzotriazolyl Carbonyl Compounds
- Other Titles
- N-하이드록시벤조트리아졸을 이용한 인아미드의 아미노산소화반응
- Author
- 임장빈
- Alternative Author(s)
- 임장빈
- Advisor(s)
- 신승훈
- Issue Date
- 2020-08
- Publisher
- 한양대학교
- Degree
- Master
- Abstract
- Addition of N-hydroxybenzotriazoles to ynamides occurred with spontaneous rearrangement into α-benzotriazolyl imides. The transformation proceeded at rt in the absence of any catalyst, but could be efficiently catalyzed by Zn(OTf)2. Crossover experiments confirmed that the rearrangement is an intramolecular process, most likely via a concerted mechanism. However, heating the mixture above 110 oC resulted in isomerization of N2- into N1-product, via heterolytic C-N bond dissociation. This tandem addition-rearrangement sequence provides an efficient and atom-economical synthetic route towards α-benzotriazolyl carbonyl compounds.
- URI
- https://repository.hanyang.ac.kr/handle/20.500.11754/152812http://hanyang.dcollection.net/common/orgView/200000438027
- Appears in Collections:
- GRADUATE SCHOOL[S](대학원) > CHEMISTRY(화학과) > Theses (Master)
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