Skip to main content

Miscellaneous Analogs

  • Chapter
  • First Online:
  • 313 Accesses

Part of the book series: SpringerBriefs in Molecular Science ((BRIEFSMOLECULAR))

Abstract

The reactions of vinylidenecyclopropanes (VDCPs) 1, which cannot be classified into the foregoing chapters, are shown in this chapter. In this chapter, Brønsted base-mediated as well as radical reaction, cycloaddition reaction and oxidation reaction of vinylidenecyclopropanes are displayed.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   34.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   49.95
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  1. Shi M, Shao LX, Lu JM, Wei Y, Mizuno K, Maeda H (2010) Chemistry of vinylidenecyclopropanes. Chem Rev 110:5883–5913

    Article  CAS  Google Scholar 

  2. Shao LX, Zhang YP, Qi MH, Shi M (2007) Lewis acid catalyzed rearrangement of vinylcyclopropenes for the construction of naphthalene and indene skeletons. Org Lett 9:117–120 (and references therein)

    Google Scholar 

  3. Lu JM, Shi M (2008) LDA-mediated selective addition reaction of vinylidenecyclopropanes with aldehydes, ketones, and enones: facile synthesis of vinylcyclopropenes, allenols, and 1,3-enynes. Org Lett 10:1943–1946

    Article  CAS  Google Scholar 

  4. Lu JM, Shi M (2009) Lithium diisopropylamide-mediated carbolithiation reactions of vinylidenecyclopropanes and further transformations of the adducts. Chem Eur J 15:6065–6073

    Article  CAS  Google Scholar 

  5. Huang JW, Shi M (2005) Carbolithiation of gem-aryl disubstituted methylenecyclopropanes. Org Biomol Chem 3:399–400

    Article  CAS  Google Scholar 

  6. Paradies J, Erker G, Fröhlich R (2006) Functional-group chemistry of organolithium compounds: photochemical [2 + 2] cycloaddition of alkenyl-substituted lithium cyclopentadienides. Angew Chem Int Ed 45:3079–3082

    Article  CAS  Google Scholar 

  7. Miller CJ, O’Hare D (2005) A new phosphine-functionalised [1]ferrocenophane and its use in the functionalisation of mesoporous silicas. J Mater Chem 15:5070–5080

    Article  CAS  Google Scholar 

  8. Chou PK, Dahlke GD, Kass SR (1993) Unimolecular rearrangements of carbanions in the gas phase. 2. Cyclopropyl anions. J Am Chem Soc 115:315–324

    Article  CAS  Google Scholar 

  9. Creary X (1977) 3,3-Dimethylallenyllithium. Reaction with electrophiles leading to carbenoid, electron transfer, and nucleophilic processes. J Am Chem Soc 99:7632–7639

    Article  CAS  Google Scholar 

  10. Moreau JL (1980) In: Patai S (ed) The chemistry of ketenes, allenes and related compounds. Wiley, New York, p 363

    Google Scholar 

  11. Huynh C, Linstrumelle G (1983) Prop-2-ynyl- and propadienyllithium reagents. Regiocontrolled synthesis of allenic compounds. J Chem Soc Chem Commun 1133–1134

    Google Scholar 

  12. Faza ON, López CS, de Lera AR (2007) Sulfoxide-induced stereoselection in [1,5]-sigmatropic hydrogen shifts of vinylallenes. A computational study. J Org Chem 72:2617–2624

    Article  Google Scholar 

  13. Lu BL, Lu JM, Shi M (2009) Butyl lithium (nBuLi)-mediated carboxylation of vinylidenecyclopropanes with CO2. Tetrahedron 65:9328–9335

    Article  CAS  Google Scholar 

  14. Lu BL, Lu JM, Shi M (2010) LDA-mediated domino carbolithiation reactions of vinylidenecyclopropanes with but-3-yn-2-one and 1-phenylprop-2-yn-1-one. Tetrahedron Lett 51:321–324

    Article  CAS  Google Scholar 

  15. Shi M, Lu JM (2006) Reactions of vinylidenecyclopropanes with diphenyl diselenide in the presence of AIBN and further transformation to produce new naphthalene derivatives. J Org Chem 71:1920–1923

    Article  CAS  Google Scholar 

  16. Shi M, Lu JM, Xu GC (2005) Ring-opening reactions of arylvinylidenecyclopropanes with diaryl diselenide upon heating: formation of 1,2-diarylselenocyclopentene derivatives. Tetrahedron Lett 46:4745–4748 (and references therein)

    Google Scholar 

  17. Maeda H, Hirai T, Sugimoto A, Mizuno K (2003) Cyclopropanation of vinylidenecyclopropanes. Synthesis of 1-(dihalomethylene)spiropentanes. J Org Chem 68:7700–7706

    Article  CAS  Google Scholar 

  18. Liu LP, Lu JM, Shi M (2007) PhI(OAc)2-mediated novel 1,3-dipolar cycloaddition of methylenecyclopropanes (MCPs), vinylidenecyclopropanes (VCPs), and methylenecyclobutane (MCB) with phthalhydrazide. Org Lett 9:1303–1306

    Article  CAS  Google Scholar 

  19. Landa A, Seoane C, Soto JL (1974) Nitrogen heteroconjugations. VI. Reactions with diazaquinones. An Quim 70:962–965

    CAS  Google Scholar 

  20. Lora-Tamayo NP, Pardo M, Soto JL (1975) Azapolycyclic compounds. X. Oxidation of diazaquinone adducts. An Quim 71:400–405

    CAS  Google Scholar 

  21. Wu L, Shi M (2010) 1,3-Dipolar cycloaddition reactions of vinylidenecyclopropane-diesters with aromatic diazomethanes generated in situ. J Org Chem 75:2296–2301

    Article  CAS  Google Scholar 

  22. Hartzler HD (1961) Carbenes from derivatives of ethynylcarbinols. The synthesis of alkenylidenecyclopropanes. J Am Chem Soc 83:4990–4996

    Article  CAS  Google Scholar 

  23. Crandall JK, Schuster T (1990) The ozonolysis of alkenylidenecyclopropanes. J Org Chem 55:1973–1975

    Article  CAS  Google Scholar 

  24. Sugita H, Mizuno K, Saito T, Isagawa K, Otsuji Y (1992) Regioselective MCPBA-oxidation of alkenylidenecyclopropanes: a convenient synthesis of 2-methylenecyclobutan-1-ones and cyclopropyl keto esters. Tetrahedron Lett 33:2539–2542

    Article  CAS  Google Scholar 

  25. Crombie L, Maddocks PJ, Pattenden G (1978) Monoterpene synthesis via alkenylidenecyclopropanes: metal reductions and peracid oxidations. Tetrahedron Lett 19:3483–3486

    Article  Google Scholar 

  26. Su CL, Huang X, Liu QY (2008) CAN-mediated highly regio- and stereoselective oxidation of vinylidenecyclopropanes: a novel method for the synthesis of unsymmetrical divinyl ketone and functional enone derivatives. J Org Chem 73:6421–6424

    Article  CAS  Google Scholar 

  27. Nair V, Balagopal L, Rajan R, Mathew J (2004) Recent advances in synthetic transformations mediated by cerium(IV) ammonium nitrate. Acc Chem Res 37:21–30

    Article  CAS  Google Scholar 

  28. Siriwardana AI, Nakamura I, Yamamoto Y (2003) Addition of hydrogen halides to alkylidenecyclopropanes: a highly efficient and stereoselective method for the preparation of homoallylic halides. Tetrahedron Lett 44:985–987

    Article  CAS  Google Scholar 

  29. Lu BL, Shi M (2011) Oxidative isomerization of vinylidenecyclopropanes to dimethylenecyclopropanes and Brønsted acid-catalyzed further transformation. Eur J Org Chem 243–248

    Google Scholar 

  30. Lee DG, Wang Z, Chandler WD (1992) Autocatalysis during the reduction of tetra-n-propylammonium perruthenate by 2-propanol. J Org Chem 57:3276–3277

    Article  CAS  Google Scholar 

  31. Roček J, Ng CS (1974) Chromium(IV) oxidation of aliphatic aldehydes. J Am Chem Soc 96:1522–1529

    Article  Google Scholar 

  32. Roček J, Ng CS (1973) The role of hydrate formation in the chromium(VI) oxidation of aldehydes. J Org Chem 38:3348–3350

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Lixiong Shao .

Rights and permissions

Reprints and permissions

Copyright information

© 2012 The Author(s)

About this chapter

Cite this chapter

Shao, L., Lu, J., Shi, M. (2012). Miscellaneous Analogs. In: Chemical Transformations of Vinylidenecyclopropanes. SpringerBriefs in Molecular Science(). Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-27573-9_5

Download citation

Publish with us

Policies and ethics