Electrochemical and H/D-Labeling Study of Oxazolino[60]Fullerene Rearrangement

	Electrochemical and H/D-Labeling Study of Oxazolino[60]Fullerene Rearrangement
	Yang WW ; Li ZJ ; Li FF ; Gao XA
刊名	journal of organic chemistry
	2011
卷号	76 期号:5 页码:1384-1389
关键词	RETRO-CYCLOADDITION REACTION 6 6 CLOSED FULLERENES FERRIC PERCHLORATE DI(ALKOXYCARBONYL)METHANO BRIDGES INDUCED ISOMERIZATION ELECTRON-TRANSFER OPEN FULLEROIDS ZERO-ORDER C-60 METHANOFULLERENES
ISSN号	0022-3263
通讯作者	gao xa
中文摘要	isomerization of an oxazoline cycle from a [6,6]- to [5,6]-junction on the c(60) sphere of dianionic [60]fullero-oxazoline (1(2-)) during a 1,4-addition is studied by electrochemistry and a stepwise addition of phch(2)br and phcd(2)br. cyclic voltammerty of the in situ generated 1(2-) shows a very unusual positive shift for the anodic peak corresponding to the oxidation of 1(2-), indicating that the c(60) cage of dianionic 1 bears only one unit negative charge due to the heterolytic cleavage of the c(60)-o bond. further study with a stepwise addition of phch(2)br and phcd(2)br, which are used to differentiate the aryl groups added at each step onto dianionic 1, shows explicitly there is an exclusive selectivity of the c-o bond for the ring-opening and ring-closure during the isomerization of the heterocycle. a reaction mechanism is proposed on the basis of the experimental results and computational calculations.
收录类别	SCI收录期刊论文
语种	英语
WOS记录号	WOS:000287636200018
公开日期	2012-06-11
内容类型	期刊论文
源URL	[http://ir.ciac.jl.cn/handle/322003/44774]
专题	长春应用化学研究所_长春应用化学研究所知识产出_期刊论文
推荐引用方式 GB/T 7714	Yang WW,Li ZJ,Li FF,et al. Electrochemical and H/D-Labeling Study of Oxazolino[60]Fullerene Rearrangement[J]. journal of organic chemistry,2011,76(5):1384-1389.
APA	Yang WW,Li ZJ,Li FF,&Gao XA.(2011).Electrochemical and H/D-Labeling Study of Oxazolino[60]Fullerene Rearrangement.journal of organic chemistry,76(5),1384-1389.
MLA	Yang WW,et al."Electrochemical and H/D-Labeling Study of Oxazolino[60]Fullerene Rearrangement".journal of organic chemistry 76.5(2011):1384-1389.