期刊
ACS CATALYSIS
卷 10, 期 1, 页码 737-742出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b04033
关键词
twisted amides; olefin metathesis; amide bonds; ring opening; ring-opening metathesis; ROMP
资金
- Rutgers Univ.
- NSF [CAREER CHE-1650766]
- ACS PRF [DNI-55549]
- NSF-MRI grant [CHE-1229030]
- Wroclaw Center for Networking and Supercomputing [WCSS159]
Selective C=C bond cleavage in twisted amides by ring-opening olefin metathesis (ROM) was accomplished. The reaction represents the third mechanism for ring opening of nonplanar amide bonds discovered. Adding to the facile hydrolytic cleavage of nonplanar N-C(O) amide bonds and sigma N-C bond scission reactions, this reaction manifold engages a peripheral reactivity principle that hinges upon ring strain energy enforced by the twisted amide bond. Considering the wide utility of ring-opening olefin metathesis reactions in various aspects of chemistry, we anticipate that this ring-opening methodology will be of broad interest and could lead to the development of ROM reactions of twisted amides as a powerful synthetic tool.
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