Synthesis of highly strained π-bowls from sumanene

Journal of the American Chemical Society

Volumn 131, Issue 31, 2009, Pages 10810-10811

  Amaya, Toru ^a   Nakata, Takuto ^a   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HIGHLY STRAINED; SUMANENE;

HYDROCARBON; SUMANENE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PYROLYSIS; SYNTHESIS;

EID: 68249152002     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9031693     Document Type: Article

References (25)

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19. The POAV angle is widely used to gauge the curvature of a given center in bowls: Haddon, R. C. J. Am. Chem. Soc. 1987, 109, 1676.
20. The details for the bowl depth and POAV are shown in Figure S1c.
21. Calculated from the crystal structure of 1.
22. Bowl-to-bowl inversion between 7a and 7b. (Chemical Equation Presented)
23. 1H NMR.
24. Bowl depth and POAV are 1.39 Å and 10.83°, which are determined from the reported crystal structure. Petrukhina, M. A.; Andreini, K. W.; Peng, L.; Scott, L. T. Angew. Chem., Int. Ed. 2004, 43, 5477.
25. Estimated to be 63.8 kcal/mol by the DFT calculation (B3LYP/6-311+G(2d,p) //B3LYP/6-31G(d,p); see Figure S3).