An Unusual C[dbnd]C Bond Cleavage with Chromium VI Reagents: Oxidation of Primary Alcohols to Ketones

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• All the new compounds gave satisfactory analytical and spectral data. The compounds 2b, 2d and 2g were obtained as diastereomeric mixtures
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• δ 1.28(s,3H,CH3), 1.64–2.4(m,2H,CH2), 2.91(t,J=7.2Hz, 2H,benzylic CH2), 3.57(d,J=2Hz,2H, OCH2), 3.82(s,3H, OCH3), 6.68–7.2(m,3H,ArH)
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• δ 1.73–2.48(m,2H,CH2), 2.8–3.08(m,2H,benzylic CH2), 3.82(d,J=5.4Hz,2H, OCH2), 3.2–3.53(m,1H), 7.04 7.4(m,4H, ArH)
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• δ 1.74–2.52(m,2H,CH2), 2.28(s,3H,Ar–CH3), 2.72–3.0(m, 2H, benzylic CH2), 3.2–3.6(m,1H), 3.8(d,J=6.3Hz, 2H, OCH2), 6.96–7.24 (m,3H,ArH)
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• δ 1.8–2.5(m,2H,CH2), 2.87(t,J=7.2Hz,2H,benzylic CH2), 3.2–3.5(m,1H), 3.8(d,J=6.3,2H, OCH2), 3.84(s,3H, OCH3), 6.84–7.24(m, 3H, ArH)
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• δ 1.72–2.4(m,2H,CH2), 2.88(t,J=6.3,2H,benzylic CH2), 3.2–3.4(m, 1H, CH), 3.76(d,J=4Hz, 2H, OCH2), 3.78(s, 3H, OCH3), 6.65–7.2(m,3H,ArH)
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• δ 1.72–.48(m,2H,CH2), 2.75–3.0(m,2H,benzylic CH2), 3.1–3.48(m, 1H), 3.77(d,J=6.3Hz,2H, OCH2), 3.87 (s,6H, OCH3), 6.78(s, 1H,ArH), 6.88(s, 1H,ArH
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• δ 1.6–2.76(m,2H,CH2), 2.76–3.1(m,2H,benzylic CH2), 3.4–3.72(m, 1H). 3.75(d,J=6.3Hz,2H, OCH2), 3.87(s,3H, OCH3), 6.6–7.2(m,3H,ArH)
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• δ 2.25–2.6(m,2H,CH2), 3.0(t,J=7Hz,2H,benzylic CH2), 3.75–4.0(m, 1H), 3.8(s,3H,OCH3), 6.6–7.3(m,3H,ArH), 9.63(d,J=2Hz,1H,CHO)
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• δ 1.7–2.75(m,2H,CH2), 3.0(t,J=7Hz,2H,benzylic CH2), 3.78(s,3H, OCH3), 6.65–7.15(m,3H,ArH), 9.45(s,1H,CHO)
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• δ 1.6–2.1(m,4H,2XCH2), 2.76(t,5.4Hz,2H,benzylic CH2), 2.86–3.1(m,1H, CH), 3.77(d,J=6.3Hz,2H, OCH2), 7.0–7.36(m, 4H, ArH)
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• δ 1.5–2.1(m,4H,2XCH2), 2.31(s,3H,Ar–CH3), 2.72(t, J=5.4Hz,2H,benzylic CH2), 2.82–3.1(m, 1H,CH), 3.8(d, J=7.2Hz,2H, OCH2), 6.8–7.16(m,3H,ArH)
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• δ 1.6–2.1(m,4H,2XCH2), 2.68(t,J=5.4Hz,2H,benzylic CH2), 2.8–3.06(m,1H), 3.78(s,3H, OCH3), 3.79(d, J=6.3Hz,2H, OCH2), 6.56–7.12(m,3H,ArH)
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• δ 1.68–2.08(m,4H,2XCH2), 2.74 (t,J=5.4Hz,2H,benzylic CH2), 2.78–3.1(m,1H), 3.77(d,J=6.3Hz,2H, OCH2), 3.97(s,3H, OCH3), 6.6–7.24(m,3H,ArH)
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• δ 1.6–2.08(m,4H,2XCH2), 2.18(s,3H,Ar–CH3), 2.65(t, J=6.3Hz, 2H, benzylic–CH2–), 2.8–3.06(m, 1H,), 3.8(s,3H, OCH3), 3.8(d,J=7.2Hz,2H, OCH2), 6.68(s, 1H, ArH), 6.86(s, 1H, ArH).
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