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Nitrile Ylides and Nitrenes from 2H-Azirines

  • Chapter
Reactive Intermediates

Abstract

2H-Azirines represent versatile substrates which can serve as useful precursors for the synthesis of other heterocyclic rings.1–7 An unusual feature of this three-membered heterocyclic ring is that it is susceptible to attack by both electrophilic and nucleophilic reagents.7 In addition, the 2π electrons present in the ring are known to participate in thermally allowed [π 2 s + π 2 s] cycloadditions as the dienophile component.8,9 Another intriguing aspect of this ring system is that it can participate as a dipolarophile in 1,3-dipolar cycloaddition reactions.10–12 Reaction with diazoalkanes10–12 and nitrile oxides10 transforms the 2H-azirine into allylic azides and carbodiimides, respectively. Few reactions rival cycloadditions in the number of bonds that undergo transformation during the reaction, producing products considerably more complex than the reactants. Cycloaddition reactions utilizing 2H-azirines include thermal reactions with ketenes,5,6 ketenimines,5 cyclopentadienones,13,14 cyclopentadiene,15 and diphenylisobenzofuran16,17 to yield a variety of unusual heterocyclic ring systems. 2H-Azirines also react photochemically with various carbon-carbon and hetero double bonds to give five-membered heterocyclic rings.18,19 The photoreaction proceeds by way of irreversible opening of the azirine ring to form a nitrile ylide intermediate which is subsequently trapped by a suitable dipolarophile.20 Products formed on thermal excitation of the 2H-azirine system, on the other hand, appear to involve vinyl nitrenes as intermediates.21–32 The intent of this chapter is to provide an indication of the wide diversity and intriguing transformations that 2H-azirines undergo upon electronic and thermal excitation. It is hoped that an overview of the major developments and potentialities in this area will be attained.

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  1. Department of Chemistry, Emory University, 30322, Atlanta, Georgia, USA

    Albert Padwa & Per H. J. Carlsen

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  1. Albert Padwa
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  1. Clemson University, Clemson, South Carolina, USA

    R. A. Abramovitch

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© 1982 Plenum Press, New York

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Padwa, A., Carlsen, P.H.J. (1982). Nitrile Ylides and Nitrenes from 2H-Azirines. In: Abramovitch, R.A. (eds) Reactive Intermediates. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-3192-6_2

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