Azizoglu, AkinDemirkol, OnurKilic, TurgutYildiz, Y. Kemal2019-08-012019-08-0120070040-4020https://dx.doi.org/10.1016/j.tet.2007.01.017https://hdl.handle.net/11480/54041-Bromo-1-fluoro-[1a,2,7,7a]-tetrahydro-1H-cyclopropa[b]naphthalene (19) has been prepared by the addition of bromolluoro-carbene to 1,4-dihydronaphthalene (18). Treatment of a solution of 19 in dry ether with MeLi afforded the tricyclic hydrocarbon 17, resulting from the intramolecular C-H insertion of carbene 16, and two dimerization products, the head-to-head 20 and head-to-tail 21 allene dimers, confirming the formation of title cycloallene 15 as a reactive intermediate. B3LYP/6-31 G(d) calculation predicts the activation barriers for insertion product 17 and allene product 15 as 3.70 and 9.52 kcal/mol, respectively. This prediction was in good agreement with our experimental results. (c) 2007 Elsevier Ltd. All rights reserved.eninfo:eu-repo/semantics/closedAccesscyclic allenescarbenesrearrangementsDFT calculationsArticle63112409241310.1016/j.tet.2007.01.0172-s2.0-33846821951Q2WOS:000244732800004Q1