Novel alkylaluminium chloride promoted [2+2] cycloaddition reactions of styrenes with 1,4-naphthoquinones and bromoquinones: A facile route to orthoquinodimethane precursors

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9397-9400

  Murphy, William S ^a   Neville, Daniel ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599679     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82974-7     Document Type: Article

References (18)

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3. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126.
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5. (d) Ahmed, S. Tetrahedron Lett. 1991, 32, 6997-7000.
6. (e) Quendo, A.; Rousseau, G. Tetrahedron Lett. 1988, 29, 6443-6446.
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9. (b) Engler, T.A.; Combrink, K.D.; Letavic, M.A.; Lynch, K.O.; Ray, J.E. J. Org. Chem. 1994, 59, 6567-6587.
10. 4 as promoter in the reactions with 1,4-naphthoquinones gave no isolable product. Our chemistry was equally applicable to 1,4-benzoquinones. For examples of photochemical [2+2] cycloadditions of 1,4-naphthoquinone with styrene see: (a) Krauch, C.H.; Farid, S. Tetrahedron Lett. 1966, 4783.
11. (b) Maruyama, K.; Otsuki, T.; Takuwa, A.; Kako, S. Bull. Inst. Chem. Res., Kyoto Univ. 1972, 50, 344.
12. 5. All new compounds gave satisfactory spectroscopic and analytical data.
13. 6. Banville, J.; Brassard, P. J. Chem. Soc., Perkin Trans, 1, 1976, 613.
14. 3a,b does not occur in these reactions since such a mechanism would result in loss of aromaticity of the aryl ring in quinone 1. No products derived from such intermediates were detected.
15. +, 57%), 172(100) and 158(44).
16. 9. For a related intramolecular 1,2-nucleophilic addition of a dienone see: Majetich, G.; Khetani, V. Tetrahedron Lett. 1990, 31, 2243-2246.
17. 10. Kraus, G.A.; On Man, T. Synth. Commun. 1986, 16, 1037-1042.
18. 11. Charlton, J.L.; Alauddin, M.M. Tetrahedron 1987, 43, 2873-2889.