期刊
TETRAHEDRON LETTERS
卷 48, 期 38, 页码 6767-6770出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.07.080
关键词
bicyclic piperazines; 1,2-bond migration; ring strain; LAH reduction; sigmatropic rearrangement
Reduction of (1R,6R)-7,9-diazabicyclo[4.2.2]dec-3-ene-8,10-dione (5) with lithium aluminum hydride gave a mixture of the expected (1R,6R)-7,9-diazabicyclo[4.2.2]dec-3-ene (2) as well as 7,9-diazabicyclo[4.3.1]dec-3-ene (3), resulting from 1,2-sigma (CC) migration of the pendant cis-2-butenyl ring. More of the rearranged product was observed in polar solvents and upon the addition of HMPA. The relief of ring strain imparted by the olefin may promote this rearrangement, as it was not observed when the olefin was reduced prior to the reduction. (c) 2007 Elsevier Ltd. All rights reserved.
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