The Journal of Organic Chemistry
Article
1d: (300 MHz, CDCl3) δ 8.02 (d, 2H), 7.22−7.59 (m, 8H), 4.62 (t,
1H), 2.26 (m, 1H), 1.87 (m, 1H), 1.35 (m, 12H), 0.88 (t, 3H); HRMS
(ESI-LC-MS) solution of 1d in hexane/acetone/acetonitrile
(25:25:50) + 0.1% formic acid) calcd C22H28O [M + Na]+
331.2030, found 331.2021.
thank Professor C. Hoff for help with the synthesis of optically
pure ADBs.
DEDICATION
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†This paper is dedicated to the memory of Professor N. J.
Procedure for Preparation of Octa Acid−guest Complex,
Photolysis and Analysis of Photoproducts. Stock solution of the
guest (1a−d) was prepared in DMSO-d6. Octa acid solution (5 mM)
was prepared in sodium tetraborate buffered D2O. Aliquots of the
guest solution were added to octa acid solution maintaining a host−
guest ratio of 2:1, and the solution was sonicated for 30 min. NMR
analysis of the solution showed formation of a complex. The solution
was then bubbled with nitrogen for 30 min and irradiated using a
medium-pressure Hg lamp for 10−30 min (to ensure at least 20−25%
conversion). The photoproducts were extracted from the aqueous
solution with chloroform and the organic layer was analyzed by GC.
Retention times of each guest and its products are as given below.
Substrate 1a. Column: HP-1, temperature program: initial temp,
70 °C; initial time, 1 min; rate, ramp 10 °C/min; ramp ends, 220 °C;
ramp time, 1 min; rate, 3 °C/min final temp, 270 °C; final time, 10
min. Retention times: 1a, 14.00 min; 4, 14.93 min; 5a, 12.56, 12.913
min; 6a, 15.52 min. Irradiation time: 15 min.
Turro, an outstanding teacher and selfless mentor.
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Substrate 1b. Column: HP-1, temperature program: initial temp,
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Substrate 1c. Column: HP-1, temperature program: initial temp, 70
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Substrate 1d. Column: HP-1, temperature program: initial temp,
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(16), 91 (14). 1d: 308 (M+, 1), 196 (8), 134 (16), 105 (100), 91 (39).
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148 (100), 133 (45), 105 (85), 91 (28). 2c: 280 (M+, 1), 262 (3), 196
(61), 148 (100), 133 (45), 105 (71), 91 (31). 2d: 308 (M+, 0), 291
(11), 205 (4), 196 (51), 148 (100), 133 (49), 105 (63), 91 (41). 6a:
210 (M+, 10), 181 (100), 105 (45). 6b: 238 (M+, 14), 196 (20), 181
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ASSOCIATED CONTENT
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S
* Supporting Information
1H NMR titration spectra, 2-D COSY and NOESY spectra of
host−guest complexes. This information is available free of
(28) Jayaraj, N.; Zhao, Y.; Parthasarathy, A.; Porel, M.; Liu, R. S. H.;
Ramamurthy, V. Langmuir 2009, 25, 10575.
AUTHOR INFORMATION
Corresponding Author
Notes
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(29) Kulasekharan, R.; Jayaraj, N.; Porel, M.; Choudhury, R.;
Sundaresan, A. K.; Parthasarathy, A.; Ottaviani, M. F.; Jockusch, S.;
Turro, N. J.; Ramamurthy, V. Langmuir 2010, 26, 6943.
(30) Tang, H.; de Oliveira, C. S.; Sonntag, G.; Gibb, C. L. D.; Gibb,
B. C.; Bohne, C. J. Am. Chem. Soc. 2012, 134, 5544.
(31) Porel, M.; Jayaraj, N.; Kaanumalle, L. S.; Maddipatla, M. V. S.
N.; Parthasarathy, A.; Ramamurthy, V. Langmuir 2009, 25, 3473.
(32) Chen, J. Y. C.; Jayaraj, N.; Jockusch, S.; Ottaviani, M. F.;
Ramamurthy, V.; Turro, N. J. J. Am. Chem. Soc. 2008, 130, 7206.
(33) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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V.R. is grateful to the National Science Foundation for
generous financial support (CHE-0848017) and for the funds
toward the purchase of a LC-ESI-MS (CHE-0946858). We
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dx.doi.org/10.1021/jo3023928 | J. Org. Chem. 2013, 78, 942−949