Generation and reactions of Pentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]non-4-ene.
Generation and reactions of Pentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]non-4-ene.
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五环[4.3.0.0(2,4).0(3,8).0(5,7)]non-4-ene的生成和反应。
DOI：
10.1021/jo0626313
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发表时间：
2007
期刊：
影响因子：
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通讯作者：
Elizabeth Loutzenhiser
中科院分区：
文献类型：
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作者：
M. Forman;Caitlin Moran;Joseph P. Herres;Jason R. Stairs;Emily C. Chopko;Anthony S. Pozzessere;Michael H. Kerrigan;C. Kelly;Lisa Lowchyj;Kerry J. Salandria;Annemarie Gallo;Elizabeth Loutzenhiser
高度金字塔化的烯烃，五环[4.3.0.0(2,4).0(3,8)]。0(5,7)]非4-烯(9)，通过处理4,5-二碘戊环[4.3.0.0(2,4).0(3,8)]生成。0(5,7)]壬烷（12）与正丁基锂和叔丁基锂。标题烯烃也作为其与1,3-二苯基异苯并呋喃、2,5-二甲基呋喃和螺[2.4]庚-4,6-二烯的Diels-Alder加合物被捕获。由9的金字塔化双键加成的烷基锂生成的产物已被分离出来并进行了充分的光谱表征。在MP2和B3LYP能级上，采用6-31G*基集，通过从头计算得到了9的几何形状、烯烃应变能、氢化热和相对HOMO/LUMO能。
The highly pyramidalized alkene, pentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]non-4-ene (9), has been generated via treatment of 4,5-diiodopentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]nonane (12) with n-butyllithium and tert-butyllithium. The title alkene has also been trapped as its Diels-Alder adduct with 1,3-diphenylisobenzofuran, 2,5-dimethylfuran, and spiro[2.4]hepta-4,6-diene. Products resulting from alkyllithium addition to the pyramidalized double bond of 9 have been isolated and fully characterized spectroscopically. The geometry, olefin strain energy, heat of hydrogenation, and relative HOMO/LUMO energies of 9 have been obtained by ab initio calculations at the MP2 and B3LYP levels using the 6-31G* basis set.