TWO STEP SYNTHESIS OF 3,7,7-TRIMETHYL-1,3,5-CYCLOHEPTATRIENE FROM Δ³-CARENE

References

• Gadras , A. , Dunoguès , J. , Galas , R. and Déléris , G. 1984 . J. Org. Chem. , 49 : 442
   Web of Science ®Google Scholar
• Déléris , G. , Kowalski , J. , Dunoguès , J. and Calas , R. 1977 . Tetrahedron Lett. , : 4211
   Web of Science ®Google Scholar
• Pillot , J. P. , Déléris , G. , Dunoguès , J. and Galas , R. 1979 . J. Org. Chem. , 44 : 3397
   Web of Science ®Google Scholar
• Déléris , G. , Dunoguès , J. and Calas , R. 1979 . Tetrahedron Lett. , : 4835
   Web of Science ®Google Scholar
• Déléris , G. , Dunoguès , J. and Gadras , A. 1984 . Tetrahedron Lett. , 25 : 2135
   Web of Science ®Google Scholar
• Géhanne , S. , Raynaud , F. , Gadras , A. and Déléris , G. 1992 . Tetrahedron , 48 : 6043
   Web of Science ®Google Scholar
• Déléris , G. , Dunoguès , J. and Gadras , A. 1988 . Tetrahedron , 44 : 4243
   Web of Science ®Google Scholar
• Déléris , G. , Gadras , A. and Dunoguès , J. 1990 . Tetrahedron , 46 : 5999
   Web of Science ®Google Scholar
• In a typical experiment, 2a or 2b (40 mmol, prepared as reported in References 7 and 8) was dissolved in 1,2‐dichlorethane (30 ml) in the presence of HMDS (25 ml) and heated at 80°C for 30 mm. The reaction mixture was then concentrated under reduced pressure (10 Torr) until only a brown solid remained. The liquid phase was then trapped with acetone/dry ice and distilled to yield 4 (4.3 g, 32 mol, 80% yield). Bp/27 torr = 67°C, 1H NMR (CDCl3, TMS ref, BRUKER WM 360) spectrum in full accordance with the one described in Reference 2; 13C NMR (CDCl3, TMS ref, BRUKER WH 90) δ ppm: 127.1 C1 or C6; 127.3 C1 or C6; 132 C1 or C5; 133.4 C2 or C2; 124, C3; 138.1 C4; 26.15 C7 or C8; 34.7, C9; 24.3, C10. Mass spectrometry (EI): m/z 134 (14.8) M', 119(100) M—CH3, 91 (32.2) tropylium, 77 C6H6+
   Google Scholar
• Manukov , E. N. , Chuiko , V. A. and Kuz'michkin , P. V. 1979 . Khim. Prir. Soedin , 6 : 783
   Google Scholar
• Günther , H. , Görtlitz , M. and Meisenheimer , H. 1974 . Org. Magn. Resonance , 6 : 388
   Google Scholar
• Yamamoto , M. , Nishikawa , K. and Aono , S. 1985 . Bull. Chem. Soc. Jap. , 58 : 3176
   Web of Science ®Google Scholar
• Alder , K. , Kaiser , K. and Schumacher , M. 1957 . Ann. Chem. , 602 : 80 E. J. Morriconi and C. F. Hummel, J. Org. Chem., 41, (3583 (1976)
   Google Scholar
• Corey , E. J. , Burke , J. H. and Remers , W. A. 1956 . J. Am. Chem. Soc. , 78 : 180
   Web of Science ®Google Scholar
• Campbell , J. R. B. , Islam , A. M. and Raphael , R. A. 1956 . J. Chem. Soc. , : 4096
   Web of Science ®Google Scholar