Construction of strained frameworks with 1,8-anthrylene units and acetylene linkers: Synthesis and structures of cyclic trimers

Chemistry Letters

Volumn 35, Issue 8, 2006, Pages 920-921

  Goichi, Michio ^a   Miyahara, Hiroaki ^a   Toyota, Shinji ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 33750697266     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2006.920     Document Type: Article

References (24)

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15. The addition of acetonitrile to the reaction system increased the isolated yield for the macrocyclization of 8. M. J. Cloninger, H. W. Whitlock, J. Org. Chem. 1998, 63, 6153.
16. +, 708.2817.
17. -1, T = 123 K, 8800 reflections, R1 = 0.038, Rw = 0.085. CCDC deposition number: 611249.
18. The structure of 1 was approximately reproduced by DFT calculations at the B3LYP/6-31G* level.
19. Bond angles at alkynic carbons are 178.5-180.0° for 3 (AM1) and 171.8-177.5° for 4 (X-ray). See Refs. 2b and 3.
20. In some highly strained cyclic alkynes or alkadiynes, bond angles at sp carbons are approximately 155° or even smaller. a) S. Eisler, R. McDonald, G. R. Loppnow, R. R. Tykwinski, J. Am. Chem. Soc. 2000, 122, 6917.
21. b) R. A. G. de Graaff, S. Gorter, C. Romers, H. N. C. Wong, F. Sondheimer, J. Chem. Soc., Perkin Trans. 2 1981, 478.
22. c) R. Gleiter, D. Kratz, W. Schäfer, V. Schehlmann, J. Am. Chem. Soc. 1991, 113, 9258.
23. E. Breitmaier, W. Voelter, Carbon-13 NMR Spectroscopy, 3rd ed., VCH, Weinheim, 1990, Chap. 4.3.
24. These signals are assignable to the 1,4-carbon atoms in the butadiynylene moiety, which usually give signals at a lower field than the 2,3-carbon atoms, see Ref. 12a.