Borontrifluoride-etherate induced rearrangement of bicyclo[2.2.2]octene-7,8-diones: An efficient synthesis of bicyclo[3.2.1]octene-2,8-diones

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8271-8272

  Nair, Vijay ^a   Anilkumar, Gopinathan ^a   Eigendorf, Guenter K ^b   Williard, Paul G ^c  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^c BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030580348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01897-7     Document Type: Article

References (9)

1. 1. For the formation of bicyclo{3.2.1}system via (a) controlled opening of cyclopropyl ketones, see Beames, D. J.; Halleday, J. E.; Mander, L. N. Aust. J. Chem. 1972, 25, 137.
2. (b) via arene photocycloaddition, see Wender, P. A.; Siggel, L.; Muss, J. W. in Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press; Oxford, 1991; Vol. 5; p 657 and references cited therein.
3. 2. Engler, T. A.; Letavic, M. A.; Reddy, J. P. J. Am. Chem. Soc. 1994, 113, 5069.
4. 3. Shizuri, Y.; Suyama, K.; Yamamura, S. J. Chem. Soc., Chem. Commun. 1986, 63.
5. 4. An isolated example of this rearrangement involving the Diels-Alder adduct of 3,5-di-tert-butyl-o-benzoquinone and cyclooctyne, although invoking an untenable mechanism has been reported. Verboom, W.; Bos, H. J. T. Recl. Trav. Chim.Pays-Bas. 1981, 100, 207.
6. 5. Nair, V.; Kumar, S.; Anilkumar, G.; Nair, J. S. Tetrahedron. 1995, 51, 9155.
7. 6. Friedrichsen, W.; Betz, M.; Buldt, E.; Jurgens, H. J., Schmidt, R.; Schwarz, I.; Visser, K. Liebigs. Ann. Chem. 1978, 440.
8. +) 322.19328; Found: 322.19270.
9. 2: C, 85.28; H, 7.61 Found: C, 85.60; H, 7.68.