Some Preparation Methods of a Tricyclo[4.1.0.0^2,7]Hept-4-En-3-One Skeleton

References

• Prinzbach , H. , Babsch , H. and Fritz , H. 1976 . Tetrahedron Lett. , : 2129
   Web of Science ®Google Scholar
• Sugihara , Y. , Morokoshi , N. and Murata , I. 1977 . Tetrahedron Lett. , : 3887
   Web of Science ®Google Scholar
• Murata , I. , Sugihara , Y. , Sugimura , T. and Wakabayashi , S. 1986 . Tetrahedron , 42 : 1745
   Web of Science ®Google Scholar
• Sugihara , Y. , Sugimura , T. and Murata , I. 1981 . J. Am. Chem. Soc. , 103 : 6738
   Web of Science ®Google Scholar
• 1984 . item, ibid , 106 : 7268
   Google Scholar
• Sugihara , Y. , Wakabayashi , S. , Saito , N. and Murata , I. 1986 . ibid , 108 : 2773
   Google Scholar
• Mancini , I. , Cavazza , M. , Guella , G. and Pietra , F. 1994 . J. C. S. Perkin Trans. 1 , : 2181
   Google Scholar
• Cavazza , M. and Pietra , F. 1986 . J. Chem. Soc., Chem. Commun. , : 1480
   Google Scholar
• Cavazza , M. , Guerriero , A. and Pietra , F. 1986 . J. Chem. Soc, Perkin Trans 1 , : 2005
   Google Scholar
• Cavazza , M. and Pietra , F. 1985 . J. Chem. Soc., Perkin Trans. 1 , : 2283
   Google Scholar
• Sugihara , Y. , Sugimura , T. , Saito , N. and Murata , I. 1989 . J. Chem. Soc. Chem. Commun. , : 537
   Google Scholar
• Trost , B. M. , Salzman , T. N. and Hiroi , K. 1976 . J. Am. Chem. Soc. , 98 : 4887
   Web of Science ®Google Scholar
• Ipaktschi , J. 1972, 1996 . Chem. Ber. , 105
   Google Scholar
• For example, l-t-butyltricyclo[4.1.0.02,7]hept-4-en-3-one was obtained as a mixture with its Dewar type isomer in a good yield. Column chromatography resulted in isomerization of this desired product to the Dewar type isomer rather than purification of the former.
   Google Scholar
• Compound 10 was prepared by photocycloaddition of 2 and methyl 3-butynoate10 in acetone as a sole cycloaddition product in a yield of 63.2 %.
   Google Scholar
• 3-Butynoic acid was prepared by addition of carbon dioxide at dry ice/ethanol temperature to a Grignard compound made from propagyl bromide, and was purified by recrystallization from a mixture of benzene and ligroin. Methyl 3-butynoate was prepared by esterification of the acid with diazomethane.
   Google Scholar
• Compound 11 was prepared by photocycloaddition of 2 and phenyl 3butynoate12 in acetone as a crystalline compound in a 13 % yield, which was a sole cycloaddition product.
   Google Scholar
• Phenyl 3-butynoate was prepared by treatment of a mixture of 3-butynoic acid and phenol in trifluoroacetic anhydride at 80°C for 40 h in a yield of 23 %.
   Google Scholar
• We examined here sodium hydride, potassium carbonate, triethylamine, 1,8-diazabicyclo[5.4.0]undecene, tetramethylammonium 2,4,6-trimethylbenzene-carboxylate,14 and diisopropylethylamine
   Google Scholar
• Volkmann , R. A. , Andrews , G. C. and Johnson , W. S. 1975 . J. Am. Chem. Soc. , 97 : 4777
   Web of Science ®Google Scholar
• Compound 16 was prepared by elimination of acetic acid of 3 with deactivated alumina (3 % H2O).
   Google Scholar
• Padwa , A. and Battisti , A. 1971 . J. Am. Chem. Soc. , 93 : 1304
   Web of Science ®Google Scholar
• Johnson , P. Y. and Berchtold , G. A. 1970 . J. Org. Chem. , 35 : 584
   Web of Science ®Google Scholar