Organic Letters
Experimental data as well as 1H and 13C NMR spectra for
Letter
(9) (a) Schick, H.; Lehmann, G.; Hilgetag, G. Chem. Ber. 1969, 102,
3238. (b) Schick, H.; Lehmann, G.; Hilgetag, G. Angew. Chem., Int. Ed.
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Chem., Int. Ed. Engl. 1967, 6, 80. (d) Schick, H.; Lehmann, G.; Hilgetag,
G. Chem. Ber. 1967, 100, 2973.
all new compounds prepared here(PDF)
AUTHOR INFORMATION
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Corresponding Author
ORCID
(10) Meister, P. G.; Sivik, M. R.; Paquette, L. A. Org. Synth. 1992, 70,
226.
(11) For a review of the synthesis of 2-alkyl-1,3-diones from
dicarboxylic acids and their derivatives, see Schick, H.; Eichhorn, I.
Synthesis 1989, 1989, 477.
Author Contributions
‡A.M.A. and S.B. contributed equally. The manuscript was
written through contributions of all authors. All authors have
given approval to the final version of the manuscript
(12) Matoba, K.; Tachi, M.; Itooka, T.; Yamazaki, T. Chem. Pharm.
Bull. 1986, 34, 2007.
(13) Sartori, G.; Bigi, F.; Baraldi, D.; Maggi, R.; Casnati, G.; Tao, X.
Synthesis 1993, 1993, 851−852.
(14) Self-condensation byproducts of acid chlorides have been
reported to result from the AlCl3-mediated Dieckmann cyclization of
dicarboxylic acids. See ref 11 and Dziomko, V. M.; Ivanov, O. V. Zh. Org.
Khim. 1967, 3, 712−717.
Notes
The authors declare no competing financial interest.
(15) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94,
7448.
ACKNOWLEDGMENTS
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(16) (a) Pines, S. H.; Douglas, A. W. J. Org. Chem. 1978, 43, 3126.
(b) Olah, G. A.; Kuhn, S. J.; Flood, S. H. J. Am. Chem. Soc. 1962, 84,
1688−1695. (c) Schmerling, L. Ind. Eng. Chem. 1948, 40, 2072−2077.
(17) We observed decreased yields upon storage of this AlCl3·MeNO2
complex, prompting us to generate it in situ.
(18) Similar patterns have been observed for other 1,3-diketones.
Additionally, poor resolution of the C1 and C3 carbon atoms is observed
even after 2000 scans for 13C NMR. For examples of similar observations
in 13C NMR, please see: (a) Ramachary, D. B.; Kishor, M. Org. Biomol.
Chem. 2008, 6, 4176−4187. (b) Ramachary, D. B.; Reddy, Y. V.; Kishor,
M. Org. Biomol. Chem. 2008, 6, 4188−4197. (c) Lacoste, E.; Vaique, E.;
Berlande, M.; Pianet, I.; Vincent, J. M.; Landais, Y. Eur. J. Org. Chem.
2007, 2007, 167−177. (d) Madhavachary, R.; Ramachary, D. B. Eur. J.
Org. Chem. 2014, 2014, 7317−7323.
(19) Crystallographic data for 28: C12H18O2 M = 194.26,
orthorhombic, space group Fdd2, a = 20.1291(4), b = 36.079(3), c =
5.96490(10) Å, V = 4332.0(3) Å3, ρcalcd = 1.191 Mg/m−3, T = 85(2) K,
reflections collected: 16521, independent reflections 1935 (R(int) =
0.0551), R(all) = 0.0277, wR(gt) = 0.0686. CCDC 1457125 contains the
supplementary crystallographic data for this paper. These data can be
obtained free of charge from The Cambridge Crystallographic Data
(20) β-Substituted acid chlorides such as 3,3-dimethylbutyryl chloride
and isovaleryl chloride primarily provided self-condensation products.
While we did not observe any 2-alkyl-1,3-dione species, we did, however,
isolate the related 2-acyl-1,3-dione products. This unexpected result
prompted us to investigate the mechanism of the reaction. See: Armaly,
This work was supported by the Petroleum Research Fund
(PRF#54688-DNI1), the University of Michigan Office of
Research, and the NSF/National Science Foundation (CHE-
1654223). A.M.A. thanks the National Science Foundation for a
Graduate Research Fellowship (Grant No. 1256260). We are
grateful to J.W. Kampf at the University of Michigan for the X-ray
crystallographic analysis of compounds 18 and 28. We thank
Prof. Rod Peakall at the Australian National University for
providing pictures of C. trapeziformis.
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