UNUSUAL BRIDGEHEAD REACTIVITY - FORMATION OF [1.1.1]PROPELLANE BY 1,3-DEHYDROBROMINATION OF 1-BROMOBICYCLO[1.1.1]PENTANE

被引:17
作者
DELLA, EW
TAYLOR, DK
TSANAKTSIDIS, J
机构
[1] School of Physical Sciences, The Flinders University of South Australia BEDFORD PARK
关键词
D O I
10.1016/S0040-4039(00)97847-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction between t-butyllithium and 1-bromobicyclo[1.1.1]pentane 4 is characterised by 1,3-dehydrobromination and gives [1.1.1]propellane 6. In the presence of t-butyllithium, 6 undergoes ring-opening and yields 3-t-butylbicyclo[l.l.1]pentyllithium 13. © 1990.
引用
收藏
页码:5219 / 5220
页数:2
相关论文
共 7 条
[1]   C-13-C-13 COUPLING-CONSTANTS IN BRIDGEHEAD POLYCYCLOALKANECARBOXYLIC ACIDS [J].
DELLA, EW ;
GANGODAWILA, H ;
PIGOU, PE .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :592-596
[2]   SYNTHESIS AND SOLVOLYSIS OF 1-BROMOBICYCLO[1.1.1]PENTANE [J].
DELLA, EW ;
TAYLOR, DK .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (05) :945-948
[3]   THE CENTRAL PROPELLANE BOND AS POLYMERIZABLE CC SINGLE BOND - POLY(TRICYCLO[4.2.0.02,7]OCTANE-1,7-DIYL) - A POLY([1.1.1]PROPELLANE) [J].
SCHLUTER, AD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (02) :296-298
[4]   [1.1.1]PROPELLANE [J].
WIBERG, KB ;
WALKER, FH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (19) :5239-5240
[5]  
WIBERG KB, 1977, J AM CHEM SOC, V99, P2297, DOI 10.1021/ja00449a045
[6]   [2.1.1]PROPELLANE - REACTION OF 1,4-DIIODOBICYCLO[2.1.1]HEXANE WITH TERT-BUTYLLITHIUM AND WITH POTASSIUM ATOMS [J].
WIBERG, KB ;
WALKER, FH ;
PRATT, WE ;
MICHL, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3638-3641
[7]   FORMATION AND REACTIONS OF 1-LITHIOBICYCLO[1.1.1]PENTANE [J].
WIBERG, KB ;
WADDELL, ST .
TETRAHEDRON LETTERS, 1988, 29 (03) :289-292