C.E. McDonald et al. / Tetrahedron 69 (2013) 2947e2953
2953
J¼6.5 Hz, 1H), 4.59 (d, J¼6.9 Hz, 1H), 4.30 (t, J¼6.9 Hz, 1H),
.76e3.66 (m, 1H), 3.51e3.37 (m, 5H), 1.60e1.48 (m, 2H), 1.48
s, 3H), 1.43e1.31 (m, 2H), 1.31 (s, 3H), 1.16 (t, J¼7.1 Hz, 3H), 0.91
2
SmI -containing flask. After stirring for 1 min, the spectrum was
acquired.
3
(
(
13
t, J¼7.3 Hz, 3H). C NMR (75 MHz)
d 112.2, 107.7, 85.3, 85.0, 82.3,
Acknowledgements
7
1.7, 71.2, 62.8, 31.7, 26.4, 25.0, 19.3, 14.9, 13.9. HRMS (ESI) m/z
þ
[MþNa] calcd for C14
26 5
H O Na 297.1672, found 297.1672.
Acknowledgement is made to the Donors of the American
Chemical Society Petroleum Research Fund for support of this
research. We also thank Lycoming College for a professional
development grant to support this work. The authors are also
indebted to Holly Bendorf, Daniel Dirocco, Ahren Green, Joseph
Keane, and Kyle Ruhl for helpful discussions.
4
d
.8.5. Cholest-5-ene (8g).43 White solid. 1H NMR (300 MHz)
5.30e5.28 (m, 1H), 2.32e2.18 (m, 1H), 2.10e1.93 (m, 3H),
1.90e1.81 (m, 2H), 1.79e1.69 (m, 1H), 1.63e0.92 (m, 23H), 1.00
(
(
5
3
s, 3H), 0.92 (d, J¼6.4 Hz, 3H), 0.90 (d, J¼1.3 Hz, 3H), 0.88
13
d, J¼1.3 Hz, 3H), 0.70 (s, 3H). C NMR (75 MHz)
d
143.7, 119.0,
6.8, 56.1, 50.6, 42.31, 39.9, 39.8, 39.5, 37.5, 36.2, 35.8, 32.9,
1.9, 31.8, 28.2, 28.0, 28.0, 24.3, 23.8, 22.8, 22.5, 20.7, 19.5,
8.7, 11.8.
Supplementary data
1
4
.8.6. 1-n-Butoxynaphthalene (8k).44 Colorless oil. 1H NMR
300 MHz) 8.21 (m, 1H), 7.70 (m, 1H), 7.40e7.24 (m, 4H), 6.69 (d,
J¼7.2 Hz, 1H), 4.04 (t, J¼6.3 Hz, 2H), 1.82 (m, 2H), 1.52 (m, 2H), 0.94
(
d
References and notes
1
3
(
1
t, J¼7.4 Hz, 3H). C NMR (75 MHz)
d 154.9, 134.5, 127.5, 126.3,
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4
1
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3
3
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7.95 (d, J¼8.2 Hz, 1H), 7.79 (d, J¼8.1Hz, 1H),
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.64 (d, J¼9.5 Hz, 1H), 7.54e7.48 (m, 1H), 7.38e7.32 (m, 1H), 7.06
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13
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1
2
18. Hall, H. J. Am. Chem. Soc. 1957, 79, 5441e5442.
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Hilmersson, G. Org. Lett. 2010, 12, 2210e2213.
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(
(
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d
7.82e7.75 (m, 3H), 7.51e7.46 (m, 1H), 7.40e7.35
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13
m, 2H), 4.18 (t, J¼6.7 Hz), 2.66 (m, 2H). C NMR (75 MHz)
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1
2
2
2
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4
2
.9. UVevis spectrum of SmI /4DPMPA complex
4. For an example see: (a) Douvris, C.; Nagaraja, C.; Chen, C.; Foxman, B.; Ozerov,
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2
2
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probe, and a background spectrum was taken. A 0.095 M solution of
SmI in THF (1.9 mL, 0.18 mmol) was added. DPMPA (182 mg,
.839 mmol) was dissolved in THF (8.0 mL), and 7.2 mL of this
solution was transferred to the SmI -containing flask. After stirring
for 1 min, the spectrum was acquired.
2
7. Bardagi, J.; Vaillard, S. E.; Rossi, R. A. Tetrahedron Lett. 2006, 47, 3149e3152.
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2
3
3
0
2
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2
/DPMPA
3
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3
ꢀ
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A 0.10 M solution of DPMPA was made by adding DPMPA
ꢁ
(
0
391 mg, 1.80 mmol) to THF (17.3 mL), cooling to 0 C and adding
.72 mL of a 2.5 M solution of n-BuLi in hexane (1.80 mmol). In
a separate flask equipped with the UVevis probe, THF was added
14.3 mL for 1:1, 12.5 mL for 2:1, 10.7 mL for 3:1, 8.9 mL for 4:1),
and a background spectrum was taken. A 0.095 M solution of SmI
4
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4
(
4
2
2
in THF (1.9 mL, 0.18 mmol) was added. The appropriate amount
4
4. Gowrisanker, S.; Sergeev, A.; Anbarasan, P.; Spannenberg, A.; Neumann, H.;
ꢀ
of the 0.10 M solution of DPMPA in THF (1.8 mL for 1:1, 3.60 mL
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