Bronsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations

CORC > 上海有机化学研究所 > 中国科学院上海有机化学研究所 > 金属有机化学国家重点实验室

	Bronsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations
	Li W(李炜) ; Shi M(施敏) ; Li YX(李玉学)
刊名	Chem.-Eur. J.
	2009
卷号	15 期号:35 页码:8852-8860
ISSN号	0947-6539
其他题名	质子酸催化的亚乙烯基环丙烷的重排反应和DFT计算
英文摘要	Diarylvinylidenecyclopropanes undergo a novel rearrangement in the presence of the Bronsted acid Tf2NH (Tf: trifluoromethanesulfonyl) to give the corresponding naphthalene derivatives in good to high yields upon heating, whereas in the presence of the Bronsted acid toluene-4-sulfonic acid (p-TSA), the corresponding triene derivatives are afforded in moderate to good yields under mild conditions. Corresponding mechanistic studies on the basis of density functional theory (DFT) with the Gaussian03 program by using the B3LYP method have revealed that the pK(a) value of the Bronsted acid, as well as the entropy and solvent effects, plays a significant role in this reaction; these factors can discriminate the differences in the reactivity and regioselectivity among the Bronsted acids used in this reaction. In the presence of Lewis acid Sn(OTf)(2), a butatrienecyclopane can produce the corresponding ring-opened products in moderate yields.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/chem.200901172
语种	英语
WOS记录号	WOS:000270045500026
公开日期	2013-01-09
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/10256]
专题	上海有机化学研究所_金属有机化学国家重点实验室
推荐引用方式 GB/T 7714	Li W,Shi M,Li YX. Bronsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations[J]. Chem.-Eur. J.,2009,15(35):8852-8860.
APA	李炜,施敏,&李玉学.(2009).Bronsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations.Chem.-Eur. J.,15(35),8852-8860.
MLA	李炜,et al."Bronsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations".Chem.-Eur. J. 15.35(2009):8852-8860.