Synthesis and reactions of 1,1-trimethylene-1H-azulenium ion

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6195-6198

  Oda, Mitsunori ^a   Sakamoto, Aya ^a   Miyatake, Ryuta ^a   Kuroda, Shigeyasu ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Carbocations; Rearrangements; Spiro compounds; Tropylium ions

Indexed keywords

AZULENE DERIVATIVE; ION; SPIRO COMPOUND;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032552126     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01273-8     Document Type: Article

References (28)

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12. 6. For other related studies on cyclobutyl carbocations, see; Kirmse W.; Landscheidt, H.; Siegfreid R. Eur. J. Org. Chem., 1998, 213-219; Peters E. N. J. Org. Chem., 1977, 42, 3015-3017; Sorensen T. S.; Miller I. J.; Ranganayakulu, K. Aust. J. Chem., 1973, 26, 311-317.
13. 6. For other related studies on cyclobutyl carbocations, see; Kirmse W.; Landscheidt, H.; Siegfreid R. Eur. J. Org. Chem., 1998, 213-219; Peters E. N. J. Org. Chem., 1977, 42, 3015-3017; Sorensen T. S.; Miller I. J.; Ranganayakulu, K. Aust. J. Chem., 1973, 26, 311-317.
14. +, 64), 168 (100), 158 (24), 155 (42), 153 (35), 145 (30), 142 (41), 129 (25), 128 (26). UV-vis (hexane); λmax (log ε) = 222(4.20), 268sh (3.45), 274sh (3.48), 279 (3.51), 308 (3.51) nm.
15. 18) independently claimed that they had been unable to reproduce the result of Chiurdoglu and the former author also indicated that the spectral data of 13, prepared by an alternative route, do not correspond to those reported by Chiurdoglu. Thus, our results, details of which will be reported elsewhere, demonstrated for the first time that direct spirobutylation of cyclopentadiene is possible.
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17. 19) in the presence of sulfuric acid. Furthermore, pouring the solution of 7 into aqueous acetone and subsequent extraction with ether gave 14 in a yield of 67% based on the cation 4.
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19. 12. Heats of formation (ΔHf, kcal/mol) were calculated as follows. 4: 238.68; 7: 217.97; 8: 237.24; and 9: 247.83. Calculations were performed with the MOPAC program (ver. 6.02) installed on an IBM RS/6800-580 workstation.
20. +, 3), 411 (17), 410 (47), 334 (29), 333 (100), 167 (27), 165 (61), 28 (89). UV-vis (hexane); λmax (log ε) = 218 (4.88), 289 (4.90), 374 (3.98), 3.63 (4.14), 381 (3.97), 563sh (2.66), 607 (2.76), 6.45sh (2.67), 633sh (2.65) nm.
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