Reaction of 1-phenylcyclooctene with NBS.: Synthesis of allylic alcohols and 1,3-dienes

被引:0
作者
Büyükkidan, B [1 ]
Budak, IG [1 ]
Ceylan, M [1 ]
机构
[1] Gaziosmanpasa Univ, Fac Sci, Dept Chem, TR-60240 Tokat, Turkey
关键词
cyclooctan-1-ylbenzene; NBS; AgClO4; vinyl bromide; 1,3-diene; allyl alcohol;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction of 1-phenylcyclooctene (3) with NBS resulted in the formation of a mixture of products (4-8). After column chromatography, we isolated the vinyl bromide 14 and 1,3-dienes 9, 10, bromo-1, 3-dienes 11, 12 and allylic alcohol 15. Reaction of the mixture (4-8) with AgClO4 afforded compounds 9, 14, 15 and alpha, beta-unsaturated ketones 21 and 22.
引用
收藏
页码:419 / +
页数:12
相关论文
共 12 条
[1]  
Ceylan M, 2002, J CHEM RES-S, P416
[2]  
Ceylan M, 2001, J CHEM RES-S, P368
[3]  
CEYLAN M, 2002, J CHEM RES M, V9, P937
[4]   HIGH-TEMPERATURE BROMINATION .6. BROMINATION OF BENZOBARRELENE [J].
DASTAN, A ;
BALCI, M ;
HOKELEK, T ;
ULKU, D ;
BUYUKGUNGOR, O .
TETRAHEDRON, 1994, 50 (35) :10555-10578
[5]   High temperature bromination .8. Bromination of homobenzonorbornadiene [J].
Dastan, A ;
Taskesenligil, Y ;
Tumer, F ;
Balci, M .
TETRAHEDRON, 1996, 52 (44) :14005-14020
[6]  
Fray G.I., 1978, CHEM CYCLOOCTATETRAE
[7]   RENAISSANCE IN CYCLOOCTATETRAENE CHEMISTRY [J].
PAQUETTE, LA .
TETRAHEDRON, 1975, 31 (23) :2855-2883
[8]   MULTIPLE FUNCTIONALIZATION OF MEDIUM-SIZED CARBOCYCLIC RINGS - FROM CYCLOOCTANONE TO A 1,5-DIALKOXYCYCLOOCTATETRAENE [J].
PAQUETTE, LA ;
WATSON, TJ ;
FRIEDRICH, D .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :776-778
[9]   REACTIONS OF ENOL ETHERS WITH CARBENES .V. REARRANGEMENTS OF DIHALOCYCLOPROPANES DERIVED FROM 6- 7- AND 8-MEMBERED CYCLIC ENOL ETHERS [J].
PARHAM, WE ;
SOEDER, RW ;
THROCKMO.JR ;
KUNCL, K ;
DODSON, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (02) :321-&
[10]   REACTIONS OF ENOL ETHERS WITH CARBENES .8. REARRANGEMENT OF DICHLOROCYCLOPROPANE DERIVED FROM 1-ETHOXYCYCLODODECENE [J].
PARHAM, WE ;
SPERLEY, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (04) :926-&