期刊
TETRAHEDRON
卷 68, 期 26, 页码 5269-5278出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.02.049
关键词
Carboryne; Styrene; Cycloaddition; Ene reaction; Dearomatization
资金
- Research Grants Council of the Hong Kong Special Administration Region [404011]
- NSFC/RGC Joint Research Scheme [N_CUHK470/10]
- Chinese University of Hong Kong
Reaction of carboryne generated from 1-I-2-Li-1,2-C2B10H10 with styrene and its derivatives has been studied. In addition to [2+2] cycloaddition reaction and/or ene reaction, an extra-annular [4+2] cycloaddition reaction is also observed, depending upon the substituents on the vinyl unit. The resulting [4+2] cycloaddition intermediates are so reactive that they immediately undergo rearomatization via either a formal 1,3-hydrogen rearrangement or dehydrogenation initiated by hydrogen abstraction with carboryne in biradical form, to give 3,4-dihydronaphtho[1,2]-o-carboranes and naphtho[1,2]-o-carboranes, respectively. In sharp contrast to that of benzyne, further additions of carboryne onto the primary cycloadducts are not observed. (C) 2012 Elsevier Ltd. All rights reserved.
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