Organic Letters
Letter
24, 1013. (g) Mojica, M. A. Ph.D. Thesis, Georgia Institute of
Technology, Atlanta, 2014.
AUTHOR INFORMATION
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Corresponding Author
ORCID
(13) For selected examples of dimerization of N-isocyanates, see:
(a) Lwowski, W.; De Mauriac, R. A.; Murray, R. A.; Lunow, L.
Tetrahedron Lett. 1971, 12, 425. (b) Reichen, W. Helv. Chim. Acta 1976,
59, 2601. For reviews, see: (c) Reichen, W. Chem. Rev. 1978, 78, 569.
(d) Wentrup, C.; Finnerty, J. J.; Koch, R. Curr. Org. Chem. 2011, 15,
1745.
(14) For selected examples, see: (a) Roveda, J.-G.; Clavette, C.; Hunt,
A. D.; Gorelsky, S. I.; Whipp, C. J.; Beauchemin, A. M. J. Am. Chem. Soc.
2009, 131, 8740. (b) Clavette, C.; Vincent Rocan, J.-F.; Beauchemin, A.
M. Angew. Chem., Int. Ed. 2013, 52, 12705. (c) Vincent Rocan, J.-F.;
Ivanovich, R. A.; Clavette, C.; Leckett, K.; Bejjani, J.; Beauchemin, A.
M. Chem. Sci. 2016, 7, 315. (d) Ivanovich, R. A.; Clavette, C.; Vincent
Rocan, J.-F.; Roveda, J.-G.; Gorelsky, S. I.; Beauchemin, A. M. Chem. -
Eur. J. 2016, 22, 7906.
(15) Allen, M. A.; Ivanovich, R. A.; Polat, D. E.; Beauchemin, A. M.
Org. Lett. 2017, 19, 6574.
(16) For a recent review of azapeptides and their synthesis, see:
Chingle, R.; Proulx, C.; Lubell, W. D. Acc. Chem. Res. 2017, 50, 1541.
(17) Hoffman, R. V.; Nayyar, N. K. J. Org. Chem. 1995, 60, 5992.
(18) Kreye, O.; Wald, S.; Meier, M. A. R. Adv. Synth. Catal. 2013, 355,
81.
(19) Trepanier, D. L.; Eble, J. N.; Harris, G. H. J. Med. Chem. 1968, 11,
357.
(20) Casper, D. M.; Burgeson, J. R.; Esken, J. M.; Ferrence, G. M.;
Hitchcock, S. R. Org. Lett. 2002, 4, 3739.
(21) Komatsu, M.; Sakai, N.; Hakotani, A.; Minakata, S.; Ohshiro, Y.
Heterocycles 2000, 52, 541−4635.
(22) (a) Mackay, D.; Pilger, C. W. Can. J. Chem. 1974, 52, 1114.
(b) Wilson, R. M.; Chow, T. J. Tetrahedron Lett. 1983, 24, 4635.
(23) Gante, J.; Neunhoeffer, H.; Schmidt, A. J. Org. Chem. 1994, 59,
6487.
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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The authors thank the University of Ottawa and NSERC for
generous financial support. A Yu scholarship to D.E.P. is also
gratefully acknowledged. The authors thank Sebastien Roy
(University of Ottawa) for exploratory work on aza-Lossen
rearrangement involving tosyl and benzoyl derivatives of N-
hydroxyureas.
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REFERENCES
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(1) For a review of natural products containing a N−N bond, see:
Blair, L. M.; Sperry, J. J. Nat. Prod. 2013, 76, 794.
(2) For reviews of hydrazines and hydrazides, see: (a) Rothgery, E. F.
Kirk-Othmer Encyclopedia Chemical Technology, 5th ed.; Wiley: New
York, 2004; Vol. 13, p 562. (b) Ragnarsson, U. Chem. Soc. Rev. 2001, 30,
205.
(3) For a review of nitrosation at nitrogen centres, see: Williams, D. L.
H. Nitrosation Reactions and the Chemistry of Nitric Oxide’ Elsevier:
Amsterdam, 2004; p 35.
(4) For selective examples of N-nitration, see: (a) Park, Y.-D.; Kim,
H.-K.; Kim, J.-J.; Cho, S.-D.; Kim, S.-K.; Shiro, M.; Yoon, Y.-J. J. Org.
Chem. 2003, 68, 9113. (b) Anikin, O. V.; Pokhvisneva, G. V.; Lipilin, D.
L.; Mezhenin, A. V.; Tartakovsky, V. A. Russ. Chem. Bull. 2009, 58,
2043.
(24) Bhatia, P. A.; Brooks, C. D. W.; Basha, A.; Ratajczyk, J. D.; Gunn,
B. P.; Bouska, J. B.; Lanni, C.; Young, P. R.; Bell, R. L.; Carter, G. W. J.
Med. Chem. 1996, 39, 3938.
(25) Nogrady, T.; Vagi, K. M. J. Org. Chem. 1962, 27, 2270.
(26) Ivanovich, R. A.; Quartus, J. A. M.; Das Neves, N.; Loiseau, F.;
Raymond, M.; Beauchemin, A. M. Manuscript submitted for
publication in The Jounnal of Organic Chemistry.
(5) For a recent review of N−N bond formation, see: Guo, Q.; Lu, Z.
Synthesis 2017, 49, 3835.
(6) (a) Greene, F. D.; Pazos, J. F. J. Org. Chem. 1969, 34, 2269.
(b) Baumgarten, H. E.; Chen, P. Y.-N.; Taylor, H. W.; Hwang, D.-R. J.
Org. Chem. 1976, 41, 3805.
(7) (a) Wang, C.; Sperry, J. Chem. Commun. 2013, 49, 4349.
(b) Rosen, B. R.; Werner, E. W.; O'Brien, A. G.; Baran, P. S. J. Am.
Chem. Soc. 2014, 136, 5571.
(8) For selective examples of metal-catalyzed N−N bond formation,
see: (a) Neumann, J. J.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed.
2010, 49, 7790. (b) Yu, D.-G.; Suri, F.; Glorius, F. J. Am. Chem. Soc.
2013, 135, 8802. (c) Stokes, B. J.; Vogel, C. V.; Urnezis, L. K.; Pan, M.;
Driver, T. G. Org. Lett. 2010, 12, 2884. (d) Zheng, Q.-Z.; Feng, P.;
Liang, Y.-F.; Jiao, N. Org. Lett. 2013, 15, 4262.
(9) For a review of the synthesis of N-acylhydrazines, see: Licandro,
E.; Perdicchia, D. Eur. J. Org. Chem. 2004, 2004, 665.
(10) For a recent review of Curtius, Schmidt, Hofmann and Lossen
rearrangements, see: Aube, J.; Fehl, C.; Liu, R.; McLeod, M. C.;
Motiwala, H. F. Comprehensive Organic Synthesis II, 2nd ed.; Elsevier:
Amsterdam, 2014; p 598.
́
(11) For selected examples of aza-Curtius reactions, see: (a) Stolle, R.
́
J. Prakt. Chem. 1927, 116, 192. (b) Stolle, R.; Nieland, H.; Merkle, M. J.
Prakt. Chem. 1927, 117, 185. (c) Scott, F. L.; Scott, M. T. J. Am. Chem.
Soc. 1957, 79, 6077. (d) Del Signore, G.; Fioravanti, S.; Pellacani, L.;
Tardella, P. A. Tetrahedron 2001, 57, 4623. (e) Verardo, G.; Venneri, C.
D.; Esposito, G.; Strazzolini, P. Eur. J. Org. Chem. 2011, 2011, 1376.
(12) For a detailed scope of the previous publications on the aza-
Lossen rearrangement, see the Supporting Information. (a) Hurd, C. D.
J. Am. Chem. Soc. 1923, 45, 1472. (b) Hurd, C. D.; Spence, L. U. J. Am.
Chem. Soc. 1927, 49, 266. (c) Tamura, Y.; Minamikawa, J.; Haruki, S.;
Ikeda, M. Synthesis 1974, 1974, 361. (d) Tserng, K.-Y.; Bauer, L. J. Org.
Chem. 1973, 38, 3498. (e) Tserng, K.-Y.; Bauer, L. J. J. Heterocycl. Chem.
1974, 11, 163. (f) Hamby, J. M.; Bauer, L. J. J. Heterocycl. Chem. 1987,
D
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