Incorporation of an allene unit into 1,4-dihydronaphthalene: generation of 1,2-benzo-1,4,5-cycloheptatriene and its dimerization
Küçük Resim Yok
Tarih
2007
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
PERGAMON-ELSEVIER SCIENCE LTD
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
1-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.
Açıklama
Anahtar Kelimeler
cyclic allenes, carbenes, rearrangements, DFT calculations
Kaynak
TETRAHEDRON
WoS Q Değeri
Q1
Scopus Q Değeri
Q2
Cilt
63
Sayı
11
