A facile rearrangement of a bisalkynylbenzil via a benzo[c]pyrylium cation

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7457-7458

  Dyker, Gerald ^a   Stirner, Wolfgang ^a   Henkel, Gerald ^a   Köckerling, Martin ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZILIC ACID DERIVATIVE; CATION; HETEROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION;

BETULACEAE;

EID: 0033570267     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01596-8     Document Type: Article

References (6)

1. W. Stirner, Dissertation, Uni-GH Duisburg 1999.
2. The bisalkyne 1 is synthesized from 2,2'-dibromobenzil (A. Terfort, H. Brunner, J. Chem. Soc., Perkin. Trans. I 1996, 1467-1479.) by a twofold Sonogashira coupling reaction with phenyl acetylene.
3. T. Sakamoto, Y. Kondo, N. Miura, K. Hayashi, H. Yamanaka, Heterocycles 1986, 24, 2311-2314.
4. 3): δ= 123.24 (d), 123.78 (d), 124.68 (d), 125.97 (d), 127.60 (s), 127.61 (d), 128.10 (d, br), 128.35 (d), 128.53 (d, 2C), 128.86 (d, br), 129.02 (d), 129.30 (d, br), 129.46 (s), 129.49 (d, 2C), 129.56 (d), 130.64 (d, br), 131.22 (s), 132.75 (s), 133.75 (d), 134.19 (d), 134.71 (s), 136.11 (s), 137.60 (s), 143.42 (s), 143.85 (s), 144.57 (s), 195.12 (s), 198.18 (s); Calc. C 87.78, H 4.42; found C 87.80, H 4.39.
5. X-ray data of compound 2 have been deposited at the Cambridge Crystallographic Data Centre (deposition number CCDC-133228). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ [Fax. (internat.)+ 44-1223/336033; E-mail: deposit@ccdc.cam.ac.uk].
6. For Diels-Alder reactions of benzo[c]pyrylium salts, see: E. Kuznetsov, I. V. Shcherbakova, A. T. Balaban, Adv. Heterocycl. Chem. 1990, 50, 157-254, especially 219-220.