By Lixiong Shao, Jianmei Lu, Min Shi
Modern natural synthesis has paid a lot recognition to the chemistry of small carbocycles. Vinylidenecyclopropanes (VDCPs), that have strained cyclopropyl workforce attached with an allene moiety and but are thermally solid and reactive elements in natural chemistry, are flexible intermediates in natural synthesis. during this quantity, Dr. Lixiong Shao, Dr. Jianmei Lu and Prof. Dr. Min Shi evaluation their investigations at the chemistry of VDCPs, typically together with the education, the reactivities upon therapy with Lewis or Brønsted acid, in addition to transition steel catalysts and a few different miscellaneous analogues. The contributions aroused a renaissance of cationic intermediates within the chemistry of VDCPs.
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Additional resources for Chemical Transformations of Vinylidenecyclopropanes
R2 1 R 3 + R R1 Ph . Ph . 41 Plausible mechanism for the formation of products 144 Ph + Ph . 42 Plausible mechanism for the formation of products 145 R1 OH 1 R R2 . OEt2-catalyzed reactions of VDCPs 1 with xanthydrol 145 36 2 Lewis or Brønsted Acid-Mediated Transformations of VDCPs OH Ph 2' Ph + . BF3 OEt2 2 3 1' 1 . OEt2-catalyzed reactions of VDCPs 1 with xanthydrol. Reprinted from Tetrahedron, Vol 66, Wei Yuan, Min Shi, Reactions of vinylidenecyclopropanes with xanthydrol and xanthenes, Pages 7104–7111, Copyright 2011, with permission from Elsevier R1 R3 .
Reprinted with the permission from Ref. . Copyright 2011 American Chemical Society R1 THF 1 + (PhSO2)2NF 60 oC, 24 h R NFSI . 2 Reactions of VDCPs 1 with NFSI F+ + (PhSO2)2N (PhSO2)2NF NFSI R1 2' F 1' 1 . 3 Plausible mechanism for the reactions of VDCPs 1 with NFSI. Reprinted from Ref. . Copyright 2011, with permission from Elsevier R1 R2 R3 . X + X2 DCE, 0-25 oC, 3 h R2 1 1 2 3 R , R , R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-FC6H4. 4 Reactions of VDCPs 1 with I2 and Br2 at 0–25 °C. Reprinted with the permission from Ref.
Adv Synth Catal 351:135–140 25. Su CL, Huang X, Liu QY, Huang X (2009) Facile synthesis of tetrahydrofurans from cycloadditions of vinylidenecyclopropanes with aldehydes and further transformations for the construction of furan, indene, and benzo[c]fluorene derivatives. J Org Chem 74:8272–8279 References 39 26. Lu JM, Shi M (2008) Lewis acid catalyzed reactions of vinylidenecyclopropanes with activated carbon-oxygen double bond: a facile synthetic protocol for functionalized tetrahydrofuran and 3,6-dihydropyran derivatives.
Chemical Transformations of Vinylidenecyclopropanes by Lixiong Shao, Jianmei Lu, Min Shi