The O-(Methoxy)aryloxazoline Route to O-substituted Benzaldehydes: Rinu C Precursors for Diterpene Synethetic

References

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• Wilson , S. R. and Mao , D. T. J. Org. Chem. , in press
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• Bergman , E. D. 1953 . Chem. Rev. , 52 : 309
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• 3a. NMR (CDCl3/TMS) δ 7.5(m,5H), 5.6(m,2H), 4.09(s,2H), 1.4 (s,6H). 3b. NMR (CDCl3/TMS) δ 7.35(m,4H), 4.05(s,2H), 3.7(m,1H), 1.35(s,6H), 1.2(d,6H). 3c. NMR (CDCl3/TMS) δ 7.6(m,1H), 7.3(m,3H), 4.03(s,2H), 2.07(m,3H), 1.36(s,6H). 3d. (E/Z isomers) NMR (CDCl3/TMS) δ 7.57(m,1H), 7.28(m,2H), 6.8(m,1/2H), 6.7(m,1/2H), 5.87(m,1H), 4.07(s,2/3H), 4.05(s,4/3H), 2.86(m,1H), 1.40(s,2H), 1.38(s,4H), 1.28(d,6H). 3e. NMR (CDCI3/TMS) δ 7.5(m,1H), 6.75(m,2H), 5.0(m,1H), 4.9(m,1H), 3.9(s,2H), 3.81(s,3H), 2.06(d,3H), 1.27(s,6H)
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• Compounds 6a 10 6b 11 6c 12 possessed spectral data identical to those reported. 6d. NMR (CDC13/TMS) δ 10.25(s,1/5H), 10.16(s,4/5H), 7.73 (s,4/5H), 7.6(s,1/5H), 7.39–7.09(m,2H), 6.73(d,lH), 5.85(m,lH), 2.81(m,lH), 1.89(d,1/5H), 1.66(d,4/5H), 1.25(d,6H). IR (neat,film) 1685 cm−1 (s), 1610 cm−1 (m). 6e. NMR (CDC13/IMS) δ 10.11(s,1H), 7.83(d,lH), 7.5–7.2(m,2H), 5.43(m,lH), 4.93(m,1H), 3.27–2.7(m,lH), 2.7(d,3H), 1.27(d, J=6.5Hz,6H). IR (neat, film) 1680 cm−1 1605 cm−1. 6f. NMR (CDCl3/TMS) δ 10.00(s,lH), 7.96(d,J=8Hz,lH), 7.0–6.73(m,2H), 5.43(m,lH), 5.0(m,lH), 3.1(s,3H). 2.2(m,3H). IR (neat,film) 1680 cm−1(s), 1560 cm−1 (m)
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• Dale , W. J. , Starr , I. and Strobel , C. W. 1961 . J. Org. Chem. , : 26 – 2225 .
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• Brown , R. F. C. and Butcher , M. 1969 . Aust. J. Chem. , 22 : 1457
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• 7b. NMR (CDCl3/TMC) δ 7.27(m,4H), 3.6(s,2H), 3.4(s,2H), 2.07(s,3H), 1.23 (d,6H), 1.17(s,6H). IR (neat, film) 3550 cm−1. (s,OH). 7c. NMR (CDCl3/TME) δ 7.6–7.1(m,4H), 5.2(m,lH), 4.8(m,lH), 3.6(s,2H), 3.4(s,lH), 3.05(s,lH), 2.03(s,6H), 1.1(s,6H). IR (neat,film) 3700 cm−1. 7e. NMR (CDCl3/TMS) δ 7.4–7.0(m,3H), 5.2(m,lH), 4.8(m,lH), 3.6(s,2H), 3.4(s,2H), 2.87(m,2H) 2.05(s,34). IR (neat, film) 3450 cm−1
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• Wilson , S. R. and Mao , D. T. 1978 . J. Amer. Chem. Soc. , 100 : 6289
   Web of Science ®Google Scholar
• Wilson , S. R. and Mao , D. T. J. Org. Chem. , in press
   Google Scholar
• Bruggink , A. and McKillep , A. 1975 . Tetrahedron , 31 : 2607
   Web of Science ®Google Scholar
• Gassman , P. G. and Balchanis , R. J. 1977 . Tetrahedron Lett. , : 2235
   Web of Science ®Google Scholar
• Gshwend , H. W. and Hamdan , A. 1975 . J. Org. Chem. , 40 : 2008
   Web of Science ®Google Scholar
• Beak , P. and Brown , R. A. 1977 . J. Org. Chem. , 42 : 1823
   Web of Science ®Google Scholar
• Meyers , A. I. , Gabel , R. and Mihelich , E. D. 1978 . J. Org. Chem. , 43 : 1372
   Web of Science ®Google Scholar
• Nordin , I. C. 1966 . J. Heterocycl. Chem. , 3 : 531
   Web of Science ®Google Scholar
• All new compounds possessed satisfactory spectral data
   Google Scholar
• Bergman , E. D. 1953 . Chem. Rev. , 52 : 309
   Web of Science ®Google Scholar
• 5.0(m,1H), 4.9(m,1H), 3.9(s,2H), 3.81(s,3H), 2.06(d,3H), 1.27(s,6H). : 6.75(m,2H) . 3a. NMR (CDCl3/TMS) δ 7.5(m,5H), 5.6(m,2H), 4.09(s,2H), 1.4 (s,6H). 3b. NMR (CDCl3/TMS) δ 7.35(m,4H), 4.05(s,2H), 3.7(m,1H), 1.35(s,6H), 1.2(d,6H). 3c. NMR (CDCl3/TMS) δ 7.6(m,1H), 7.3(m,3H), 4.03(s,2H), 2.07(m,3H), 1.36(s,6H). 3d. (E/Z isomers) NMR (CDCl3/TMS) δ 7.57(m,1H), 7.28(m,2H), 6.8(m,1/2H), 6.7(m,1/2H), 5.87(m,1H), 4.07(s,2/3H), 4.05(s,4/3H), 2.86(m,1H), 1.40(s,2H), 1.38(s,4H), 1.28(d,6H). 3e. NMR (CDCI3/TMS) δ 7.5(m,1H)
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• Compounds 6a 10 6b 11 6c 12 possessed spectral data identical to those reported. 6d. NMR (CDC13/TMS) δ 10.25(s,1/5H), 10.16(s,4/5H), 7.73 (s,4/5H), 7.6(s,1/5H), 7.39–7.09(m,2H), 6.73(d,lH), 5.85(m,lH), 2.81(m,lH), 1.89(d,1/5H), 1.66(d,4/5H), 1.25(d,6H). IR (neat,film) 1685 cm−1 (s), 1610 cm−1 (m). 6e. NMR (CDC13/IMS) δ 10.11(s,1H), 7.83(d,lH), 7.5–7.2(m,2H), 5.43(m,lH), 4.93(m,1H), 3.27–2.7(m,lH), 2.7(d,3H), 1.27(d, J=6.5Hz,6H). IR (neat, film) 1680 cm−1 1605 cm−1. 6f. NMR (CDCl3/TMS) δ 10.00(s,lH), 7.96(d,J=8Hz,lH), 7.0–6.73(m,2H), 5.43(m,lH), 5.0(m,lH), 3.1(s,3H). 2.2(m,3H). IR (neat,film) 1680 cm−1(s), 1560 cm−1 (m)
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• 3a. NMR (CDCl3/TMS) δ 7.5(m,5H), 5.6(m,2H), 4.09(s,2H), 1.4 (s,6H). 3b. NMR (CDCl3/TMS) δ 7.35(m,4H), 4.05(s,2H), 3.7(m,1H), 1.35(s,6H), 1.2(d,6H). 3c. NMR (CDCl3/TMS) δ 7.6(m,1H), 7.3(m,3H), 4.03(s,2H), 2.07(m,3H), 1.36(s,6H). 3d. (E/Z isomers) NMR (CDCl3/TMS) NMR (crx;.l&MS) 6 7.4–7.0(m,3H), 5.2(m,lH), 4.8(m,lH), 3.6(2), 3.4(s,W), 2.87(m,2), 2.05(s,js). Ift (neat, film) 3450 cm−.
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