By Lixiong Shao, Jianmei Lu, Min Shi
Modern natural synthesis has paid a lot realization to the chemistry of small carbocycles. Vinylidenecyclopropanes (VDCPs), that have strained cyclopropyl team hooked up with an allene moiety and but are thermally good 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 overview their investigations at the chemistry of VDCPs, typically together with the instruction, the reactivities upon remedy 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 info for Chemical Transformations of Vinylidenecyclopropanes
For the mechanism of the 1,3-proton shift, see: Carey FA, Sundburg RJ (1990) Advanced organic chemistry. 3rd edn. Plenum Press, New York, pp 609–613 19. Shi M, Wu L, Lu JM (2008) Gold(I)-catalyzed intramolecular rearrangement of vinylidenecyclopropanes. J Org Chem 73:8344–8347 20. Li W, Shi M, Li YX (2009) Brønsted acid mediated novel rearrangement of diarylvinylidenecyclopropanes and mechanistic investigations based on DFT calculations. Chem Eur J 15:8852–8860 21. Huang X, Su CL, Liu QY, Song YT (2008) A facile access to medium- and large-size naphthalenacarbocycles via Lewis acid mediated ring-expansion reaction of bicyclic vinylidenecyclopropanes.
R2 OH R7 8 R + Ph Sc(OTf)3 R1 DCE, 40 oC MeO 114a R7 = R8 = 4-MeOC6H4 1 R1, R2 = 4-FC6H4, 31 Ph 4-MeC6H4, 4-ClC6H4, 2,3-Cl2C6H3, Ph 122, 50-98% OMe -H+ R2 R1 R R2 . 34 Lewis acid-catalyzed reactions of VDCPs 1 with 1,1,3-triarylprop-2-yn-1-ol 114a 3 R 1 R R + 5 1 R 1 R . 35 Nb(OTf)3-catalyzed reactions of VDCPs 1 with enynols 126 When N-(4-hydroxy-4,4-diarylbut-2-ynyl)-4-methyl-N-prop-2-ynylbenzene-sul fonamides (1,6-diynes) 141 and N-allyl-N-(4-hydroxy-4,4-diarylbut-2-ynyl) -4-methylbenzenesulfonamides (1,6-enynes) 142 were tested as the partners, the reactions with VDCPs 1 can produce polycyclic compounds 143 and 144 as well as isopropylidene-3,3-diarylcyclobut-1-enyl-methyl derivatives 145 in good to high yields depending on the substituents on VDCPs 1 and substrates 141 and 142 .
2] and [5 ? 2+1] cycloadditions of allenes and vinylcyclopropanes. J Am Chem Soc 127:6530–6531 11. Brummond KM, Chen HF, Mitasev B, Casarez AD (2004) Rhodium(I)-catalyzed ene-allene carbocyclization strategy for the formation of azepines and oxepines. Org Lett 6:2161–2163 12. Yu ZX, Cheong PHY, Liu P, Legault CY, Wender PA, Houk KN (2008) Origins of differences in reactivities of alkenes, alkynes, and allenes in [Rh(CO)2Cl]2-catalyzed (5 ? 2) cycloaddition reactions with vinylcyclopropanes. J Am Chem Soc 130:2378–2379 Chapter 4 Reactions of VDCPs with Electrophiles Abstract Reactions of vinylidenecyclopropanes with a variety of electrophiles such as diaryl diselenide, iodine, bromine, N-fluorodibenzenesulfonimide (NFSI), and N-bromosuccinimide are shown in this chapter.