References
- Deshpande , M. N. , Wehrli , S. , Jawdosiuk , M. , Guy , J. T. , Bennett , D. W. , Cook , J. M. , Depp , M. R. and Weiss , U. 1986 . J. Org. Chem. , 51 : 2436 For the use of 3-cyclopenteneglyoxal to prepare the bicyclo [3.3.0]octane ring system, see:
- Lipshutz , B. H. and Morey , M. C. 1983 . J. Org. Chem. , 48 : 3745 Imidazoles:.Pteridines: Rosowsky, A.; Chen, K. K. N. J. Org. Chem. 1973, 38, 2073.
- Ireland , R. E. and Norbeck , D. W. 1985 . J. Org. Chem. , 50 : 2198 Aliphatic α-keto aldehydes are quite prone to polymerization, hydration, and air oxidation. See: and references therein.
- Raucher , S. and Gustavson , L. M. 1986 . Tetrahedron Lett. , 27 : 1557 For an elegant approach to certain monoprotected glyoxals with control of regiochemistry, see:
- The methodology detailed in reference 1 is not convenient for large scale synthesis of glyoxals since it requires use of diazomethane.
- Bernard , D. , Doutheau , A. and Gore , J. 1987 . Tetrahedron , 43 : 2721 Certain nonaromatic glyoxals can be prepared starting with ethyl diethoxyacetate. See
- Babler , J. H. and Marcuccilli , C. J. 1987 . Tetrahedron Lett. , 28 : 4657
- Perrine , T. D. and May , E. L. 1954 . J. Org. Chem. , 19 : 773
- Brown , H. C. and Garg , C. P. 1964 . J. Am. Chem. Soc. , 86 : 1085
- This nitrile was prepared by the method described in reference 7.
- Prolonged exposure to aqueous acetic acid resulted in decomposition of 5
- Verhe , R. , Courtheyn , D. , De Kimpe , N. , De Buyck , L. and Schamp , N. 1982 . Synthesis , : 667 Aldehyde 5a was previously obtained as a minor product during the synthesis of the regioisomeric 1, 1-diethoxy-2-butanone. See:
- 1H NMR: δ (CDCl3) 9.59 (s, CHO), 3.56 (quartet, J = 7Hz, 2 × OCH2CH3), 1.85 (quartet, J = 8Hz, CH2CH3), 1.25 (t, J = 7Hz, 2 × OCH2CH3), 0.82 (t, J = 8Hz, CH2CH3).
- Raulet , C. and Levas , E. 1969 . Compt. Rend. Acad. Sci. Ser. C. , 269 : 996