Abstract
A highly reactive member of the nitrilium betaine 1,3-dipole family, the nitrile
imine is a versatile species with a wide array of applications ranging from chemical
synthesis to biorthogonal ligation and materials chemistry. The promiscuous
reactivity of the dipole with a range of nucleophiles, in addition to more conventional dipolarophiles, affords the nitrile imine a unique set of properties with
exceptional synthetic utility. This manuscript aims to provide a comprehensive
overview of the nitrile imine 1,3-dipole, from its initial discovery in 1959, through
to the most recent publications as of June 2019. Topics covered include the core
properties of the dipole and the different methods of synthesis available to chemists.
Particular attention is paid to the diverse reactivity profile of the nitrile imine and its
numerous applications in a diverse range of fields.
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A highly reactive member of the nitrilium betaine 1,3-dipole family, the nitrile
imine is a versatile species with a wide array of applications ranging from chemical
synthesis to biorthogonal ligation and materials chemistry. The promiscuous
reactivity of the dipole with a range of nucleophiles, in addition to more conventional dipolarophiles, affords the nitrile imine a unique set of properties with
exceptional synthetic utility. This manuscript aims to provide a comprehensive
overview of the nitrile imine 1,3-dipole, from its initial discovery in 1959, through
to the most recent publications as of June 2019. Topics covered include the core
properties of the dipole and the different methods of synthesis available to chemists.
Particular attention is paid to the diverse reactivity profile of the nitrile imine and its
numerous applications in a diverse range of fields.
vii