Beilstein J. Org. Chem. 2016, 12, 1081–1095.
6. Gunther, A.; Karl, T.; Harley, P.; Wiedinmyer, C.; Palmer, P. I.;
Geron, C. Atmos. Chem. Phys. 2006, 6, 3181–3210.
the dearth of convenient protocols capable of generating struc-
ture and function diverse monoterpene and sesquiterpene
nitrates.
7. Vickers, C. E.; Gershenzon, J.; Lerdau, M. T.; Loreto, F.
8. Werner, G.; Kastler, J.; Looser, R.; Ballschmiter, K.
Angew. Chem., Int. Ed. 1999, 38, 1634–1637.
Finally, the kinetics and measurement of the IPNs generated
within this study and their relationship to aspects of atmos-
pheric chemistry have been reported [56].
9. Emmerson, K. M.; Evans, M. J. Atmos. Chem. Phys. 2009, 9,
Conclusion
Isoprene, monoterpene and sesquiterpene nitrates are gaining
recognition for their significant roles in climate chemistry how-
ever an efficient route to their synthesis has yet to be developed.
Here we report an efficient silver nitrate mediated synthesis
procedure that is broadly applicable to the production of sought-
after ‘isoprene nitrates’. The general applicability of this proce-
dure has also been confirmed via its application to the first syn-
thesis of a monoterpene nitrate derived from (1R,5S)-(−)-
myrtenol. In the former examples our protocol proceeds via the
application of Horner–Wadsworth–Emmons Chemistry that
generates readily functionalized motifs that undergo an all but
previously non-existent, allylic ‘halide for nitrate’ substitution
reaction. A consequence of the broader importance of organic
nitrates we envisage our ‘halide for nitrate’ synthesis transfor-
mation will be of considerable interest to, not only atmospheric
chemists, but also the wider synthetic and medicinal chemistry
communities.
10.Teng, A. P.; Crounse, J. D.; Lee, L.; St. Clair, J. M.; Cohen, R. C.;
Wennberg, P. O. Atmos. Chem. Phys. 2015, 15, 4297–4316.
11.Xiong, F.; McAvey, K. M.; Pratt, K. A.; Groff, C. J.; Hostetler, M. A.;
Lipton, M. A.; Starn, T. K.; Seeley, J. V.; Bertman, S. B.; Teng, A. P.;
Crounse, J. D.; Nguyen, T. B.; Wennberg, P. O.; Misztal, P. K.;
Goldstein, A. H.; Guenther, A. B.; Koss, A. R.; Olson, K. F.;
de Gouw, J. A.; Baumann, K.; Edgerton, E. S.; Feiner, P. A.; Zhang, L.;
Miller, D. O.; Brune, W. H.; Shepson, P. B. Atmos. Chem. Phys. 2015,
12.Schwantes, R. H.; Teng, A. P.; Nguyen, T. B.; Coggon, M. M.;
Crounse, J. D.; St. Clair, J. M.; Zhang, X.; Schilling, K. A.;
Seinfeld, J. H.; Wennberg, P. O. J. Phys. Chem. A 2015, 119,
13.Pye, H. O. T.; Luecken, D. J.; Xu, L.; Boyd, C. M.; Ng, N. L.;
Baker, K. R.; Ayres, B. R.; Bash, J. O.; Baumann, K.; Carter, W. P. L.;
Edgerton, E.; Fry, J. L.; Hutzell, W. T. D.; Schwede, B.; Shepson, P. B.
Environ. Sci. Technol. 2015, 49, 14159–14203.
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Supporting Information
16.Crounse, J. D.; Knap, H. C.; Ørnso, K. B.; Jørgensen, S.; Paulot, F.;
Kjaergaard, H. G.; Wennberg, P. O. J. Phys. Chem. A 2012, 116,
Supporting Information File 1
Experimental.
17.Lockwood, A. L.; Shepson, P. B.; Fiddler, M. N.; Alaghmand, M.
Atmos. Chem. Phys. 2010, 10, 6169–6178.
18.Kames, J.; Schurath, U.; Flocke, F.; Volz-Thomas, A. J. Atmos. Chem.
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