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.
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References
Shi M, Shao LX, Lu JM, Wei Y, Mizuno K, Maeda H (2010) Chemistry of vinylidenecyclopropanes. Chem Rev 110:5883–5913
Shi M, Lu JM (2005) Reactions of vinylidenecyclopropanes with diaryl diselenide catalyzed by iodosobenzene diacetate and further transformation of the adducts. Synlett 2352–2356
Jiang M, Shi M (2009) Reactions of methylenecyclopropanes and vinylidenecyclopropanes with N-fluorodibenzenesulfonimide. Tetrahedron 65:5222–5227
Eberson L, Persson O (1997) Fluoro spin adducts and their modes of formation. J Chem Soc Perkin Trans 2:893–898
Jung ME, Toyota A (2001) Preparation of 4′-substituted thymidines by substitution of the thymidine 5′-esters. J Org Chem 66:2624–2635
Hill B, Liu Y, Taylor SD (2004) Synthesis of α-fluorosulfonamides by electrophilic fluorination. Org Lett 6:4285–4288
Shi M, Ma M, Shao LX (2005) Ring-opening reactions of diarylvinylidenecyclopropanes by iodine and bromine. Tetrahedron Lett 46:7609–7613
Shi M, Ma M, Zhu ZB, Li W (2006) Reactions of arylvinylidenecyclopropanes with bromine and iodine. Synlett 1943–1947
Shi M, Li W (2007) Reactions of diarylvinylidenecyclopropanes with bromine at −100 °C in dichloromethane and ether. A drastic solvent effect. Tetrahedron 63:6654–6660
Li W, Shi M (2008) An efficient method for the synthesis of vinylbromohydrin and vinylbromoalkoxy derivatives and cyclocarbonylation of α-allenic alcohols catalyzed by palladium chloride. J Org Chem 73:6698–6705
Su CL, Cao J, Huang X, Wu LL, Huang X (2011) Regiocontrolled halohydroxylations of bicyclic vinylidenecyclopropanes: a versatile strategy for the construction of diverse highly functionalized carbocyclic scaffolds. Chem Eur J 17:1579–1585
Djerassi C, Scholz CR (1947) The bromination of 3-ketosteroids in acetic acid and the effect of trace substances in the solvent. J Am Chem Soc 69:2404–2410
Cabaj JE, Kairys D, Benson TR (2007) Development of a commercial process to produce oxandrolone. Org Process Res Dev 11:378–388
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Shao, L., Lu, J., Shi, M. (2012). Reactions of VDCPs with Electrophiles. In: Chemical Transformations of Vinylidenecyclopropanes. SpringerBriefs in Molecular Science(). Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-27573-9_4
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DOI: https://doi.org/10.1007/978-3-642-27573-9_4
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