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Synthesis 2014; 46(18): 2383-2412
DOI: 10.1055/s-0034-1378662
review
© Georg Thieme Verlag Stuttgart · New York

Nitroalkynes: A Unique Class of Energetic Materials

G. Kenneth Windler*
a   College of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA   Fax: +1(510)6435208   Email: kpcv@berkeley.edu
b   High Explosives Application Facility, Lawrence Livermore National Laboratory, Livermore, CA 94550, USA
,
Philip F. Pagoria
b   High Explosives Application Facility, Lawrence Livermore National Laboratory, Livermore, CA 94550, USA
,
K. Peter C. Vollhardt*
a   College of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA   Fax: +1(510)6435208   Email: kpcv@berkeley.edu
› Author Affiliations
Further Information

Publication History

Received: 18 April 2014

Accepted: 23 April 2014

Publication Date:
26 August 2014 (online)

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We dedicate this paper to the memory of Professor H. G. Viehe, whose work on hetero-substituted and electron-poor alkynes was the inspiration for this review and our own investigations in the area.

Abstract

Forty-five years after their first preparation, nitroalkynes retain interest for their unique chemical behavior and their potential as energetic materials. This review encompasses the physical and spectral properties, synthesis, reactivity, metal complexes, and theoretical studies of nitroalkynes not previously reviewed, and those prepared after 1973.

1 Introduction

2 Physical Properties of Nitroalkynes

3 Spectral Properties of Nitroalkynes

4 Syntheses of Nitroalkynes

4.1 Unsuccessful Attempts

4.1.1 Nitration

4.1.2 Elimination

4.1.3 Retrocycloaddition

4.2 Successful Strategies

4.2.1 Nitration

4.2.2 Elimination

4.2.3 Nucleophilic Displacement

4.2.4 From Triazoles

4.3 Attempts at the Synthesis of Dinitroacetylene

5 Reactions of Nitroalkynes

5.1 Thermal Decomposition

5.2 Nucleophilic Addition

5.3 Cycloaddition

6 Metal Complexes

7 Theoretical Studies

8 Conclusion

Key words

alkynes - cycloaddition - cycloreversion - nitration - elimination - nucleophilic addition - organic explosives