3
References and notes
Supplementary Material
1
.
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1, 7223-7226; b) Debabov, V. G.; Yanenko, A. S. Review
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Supplementary data (General experimental details,
Experimental procedures for Method A and B, Spectroscopic
3
1
characterization data for the products 2a-i and 3a-l, Copies of H
1
3
and C NMR spectra for compounds 2a-i and 3a-l, Chiral
GC/MS analyses of compounds 3g-3g′ and of a mixture of 3g
and 3g′) can be found in the online version of this article.
2
007, 48, 1447-1450; e) Kamitanaka, T; Yamamoto, K; Matsuda,
T.; Harada, T. Tetrahedron 2008, 64, 5699–5702.
2
3
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2
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3
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2
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Synthesis of benzonitrile (3a): TLC (CHCl /Et
) δ: 7.73-6.98 (m,
) δ: 132.8, 132.2, 129.1,
9
1
.
3
2
O
1
9
5
1
5
0:10 v/v) Rf 0.80; H NMR (300 MHz, CDCl
3
13
H, ArH); C NMR (75 MHz, CDCl
3
+.
18.9, 112.4; GC/MS (EI) m/z (% rel.): 103[M ] (100), 76(29),
0(10).
0. Synthesis of oximes 2a-i. General procedure: A mixture of
aldehyde 1a-i (1 mmol), hydroxylamine hydrochloride (1 mmol)
and pyridine (1 mmol) in ethanol (2 mL) was heated at 60 °C for 1
hour. EtOH was then evaporated at reduced pressure. The
resulting mixture was treated with a 5% aqueous solution of
NaHSO
4
(3 mL) and extracted with CH
2
Cl
2
(3 × 5 mL). The
SO ). After
organic extracts were washed with brine and dried (Na
2
4
solvent removal at reduced pressure the corresponding oximes 2a-
i were recovered in high yields (70-96%) as a mixture of E- and Z-
isomers.
1
1. Lehnert, W. Tetrahedron Lett. 1971, 6, 559-560.