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Bromination of (1RS,2RS,5RS)-2,3-dibromo-6,7-benzobicyclo[3.2.1]octa-3,6-diene. A new and convenient synthesis of disubstituted benzobarrelenes

✍ Scribed by Cakmak, Osman; Balci, Metin

Book ID
125485323
Publisher
American Chemical Society
Year
1989
Tongue
English
Weight
882 KB
Volume
54
Category
Article
ISSN
0022-3263

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w4o-4ozO/n 53.00+ .Q) 0 19aaRrpmonhap& tion at OΒ°C producd nbhrtirrangad trfbromfdes beside tha reuunged tribroaide dnd the ketoD 12. The structures of the products wdre d8tmaincd by IH-, 13C-MfR dam and. gingh X-r& JtruCturdl MdlySiS. The addftipn wcbamsrr, is discussed in tcrhs # cro-and endo-dtta

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SUMMA??Y: Treatment of 3-bromo-6,7-benzobicyclo c3.2.11 octa-2,3-diem? (9) with potassium tert.-butoxide produces the strained bicyclic allene (10) which is trapped by 1,3-diphenylbenzo[c]furan (DBI) to give five isomeric cycloadducts. In the absence of DBI, allene (10) gave rise to enol ether ( 18)