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Synfacts 2010(2): 0171-0171
DOI: 10.1055/s-0029-1219072
DOI: 10.1055/s-0029-1219072
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Cyclotetramer of a Strained Cyclic Allene
T. Mahlokozera, J. B. Goods, A. M. Childs, D. M. Thamattoor*
Colby College, Waterville, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Januar 2010 (online)

Significance
The authors isolated compound 3 from the Doering-Moore-Skattebøl reaction of 1,1-dibromo-1a,9b-cyclopropa[l]phenanthrene (1) through the strained cyclic allene intermediate 2. The reaction described is formally a [2+2+2+2] reaction; however, the authors propose that the product is more likely formed by two sequential dimerizations due to the entropic cost of the concerted mechanism. Such cyclotetramerizations of allenes are rare in the literature and have never been reported with a seven-membered cyclic allene.