CLEAR-CUT EXAMPLE OF PREFERENCE FOR A 6-MEMBERED RING RADICAL CYCLIZATION OVER THE HOMOLOGOUS 5-MEMBERED RING RADICAL CYCLIZATION - THE REACTION OF 5-[BROMOALKYL]-5H-DIBENZO[A,D]CYCLOHEPTENE WITH BU(3)SNH

Authors
HADA C BANCIU MD MATTALIA JM CHANON M
Citation
C. Hada et al., CLEAR-CUT EXAMPLE OF PREFERENCE FOR A 6-MEMBERED RING RADICAL CYCLIZATION OVER THE HOMOLOGOUS 5-MEMBERED RING RADICAL CYCLIZATION - THE REACTION OF 5-[BROMOALKYL]-5H-DIBENZO[A,D]CYCLOHEPTENE WITH BU(3)SNH, Tetrahedron letters, 37(22), 1996, pp. 3845-3848
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
22
Year of publication
1996
Pages
3845 - 3848
Database
ISI
SICI code
0040-4039(1996)37:22<3845:CEOPFA>2.0.ZU;2-E
Abstract
The radical cyclisation reaction of the 5-[2-bromo-ethyl]-5H-dibenzo[a ,d]cycloheptene 4 with Bu(3)SnH and AIBN led to the cyclised hydrocarb on 5 as major product, whereas the bromo-derivative 8 with Bu(3)SnH an d AIBN gave only the straight chain product 9. An explanation based on the conformational rigidity of dibenzo[a,d]cycloheptene system calcul ated by AM1 method is proposed. Copyright (C) 1996 EIsevier Science Lt d