AN UNUSUAL THIOKETAL FORMATION - ATTEMPTED SYNTHESIS OF 2,3-DIBROMO-6,7-BENZOBICYCLO[3.2.1]OCTA-2,6-DIENE

Authors
TASKESENLIGIL Y BALCI M
Citation
Y. Taskesenligil et M. Balci, AN UNUSUAL THIOKETAL FORMATION - ATTEMPTED SYNTHESIS OF 2,3-DIBROMO-6,7-BENZOBICYCLO[3.2.1]OCTA-2,6-DIENE, Tetrahedron, 51(29), 1995, pp. 7993-7998
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
29
Year of publication
1995
Pages
7993 - 7998
Database
ISI
SICI code
0040-4020(1995)51:29<7993:AUTF-A>2.0.ZU;2-E
Abstract
Treatment of 8 with 2 equiv. of NBS gave tetra bromide 9 which was con verted to the corresponding unsaturated ketone 7. Reaction of 7 with 1 ,2-ethanedithiol produced the unusual thioketal 14 besides normal keta lization product 13. Reduction of 13 with Raney nickel resulted in the formation of hydrocarbon 17, instead of the expected dibromide 4.