期刊
TETRAHEDRON LETTERS
卷 56, 期 43, 页码 5870-5873出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.09.002
关键词
Acyloxy nitroso compounds; Cyclic hydroxamic acids; Ring expansion; Organic phosphines; HNO donors
资金
- National Institutes of Health [HL62198]
- Egyptian Government studentship
Treatment of cyclopentanone and cyclobutanone-derived oximes with lead(IV) tetraacetate gives the bright blue acyloxy nitroso compounds, which upon basic hydrolysis yields the ring expansion product cyclic hydroxamic acids in 12-81% yield. Reactions of substituted cyclopentanones provide ring expanded products where the -NOH group regioselectively inserts to the more substituted position and gives a better yield compared to the treatment of the same ketone with a basic solution of Piloty's acid. Reaction of phosphines with acyloxy nitroso compounds generally generates a ring-expanded Beckmann rearrangement product that can be hydrolyzed to the corresponding lactam. Acyloxy nitroso compounds that undergo rapid hydrolysis to HNO do not show this ring expansion reactivity. These results further demonstrate the versatility of acyloxy nitroso compound to yield structurally complex materials. (C) 2015 Elsevier Ltd. All rights reserved.
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