Synthesis of acid-resistant p-quinone monoketals and thermally stable 4,4-dialkoxycyclohexa-2,5-dien-1-ols

Synthetic Communications

Volumn 30, Issue 5, 2000, Pages 877-885

  Omura, Kanji ^a  

^a KOSHIEN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; REACTION ANALYSIS; REACTION TIME; REDUCTION; STEREOSPECIFICITY; SYNTHESIS; THERMOSTABILITY;

EID: 0034062235     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008087100     Document Type: Article

References (12)

1. a) Swenton, J. S. Acc. Chem. Res. 1983, 16, 74.
2. b) Fujita, S. Yuki Gosei Kagaku Kyokaishi 1982, 40, 307.
3. Swenton, J. S. In The Chemistry of Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1988; Part 2, Vol. 2, p 899.
4. Omura, K. Synthesis 1998, 1145.
5. Nilsson, A.; Palmquist, U.; Pettersson, T.: Ronlán, A. J. Chem. Soc., Perkin Trans. 1 1978, 708.
6. The melting point of 1a is reported to he 143.5-145 °C, while that obtained by us melted at 166-167 °C. It is presumable that 1a from the electrochemical method has not been purified rigorously.
7. Büchi, G.; Chu, P.-S.; Hoppmann, A.; Mak, C.-P.; Pearce, A. J. Org. Chem. 1978, 43, 3983.
8. McKillop, A.; Perry, D. H.; Edwards, M.; Antus, S.; Farkas, L; Nógrádi, M. J. Org. Chem. 1976, 41, 282.
9. Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
10. Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891
11. Henton, D. R.; Anderson, K.; Manning, M. J.; Swenton, J. S. J. Org. Chem. 1980, 45, 3422.
12. Kornblum, N.; Seltzer, R. J. Am. Chem. Soc. 1961, 83, 3668.