The Friedel-Crafts Chemistry: Acetates of the Baylis-Hillman Adducts as Novel Stereodefined β-Electrophiles

Synlett

Volumn 1996, Issue 4, 1996, Pages 393-395

  Basavaiah, D ^a   Pandiaraju, S ^a   Padmaja, K ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000695725     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5422     Document Type: Article

References (17)

1. Olah, G.A. (Editor), Friedel-Crafts Chemistry, Wiley, New York, 1973.
2. Olah, G.A.; Krishnamurti, R.; Prakash, G.K.S. in Comprehensive Organic Synthesis, 1990, vol 3, p 293 (Trost, B.M.and Fleming, I. Editors), Pergamon Press., New York and references cited therein.
3. Sha, C-K; Young, J.-J; Yeh, C-P; Chang, S-C; Wang, S-L. J. Org. Chem., 1991, 56, 2694
4. Basavaiah, D.; Sarma, P.K.S. J. Chem. Soc. Chem. Commun., 1992, 955.
5. Basavaiah, D; Sarma, P.K.S; Bhavani, A.K.D. J. Chem. Soc. Chem. Commun., 1994, 1091.
6. Basavaiah, D.; Gowriswari, V.V.L. Tetrahedron Lett., 1986, 27, 2031.
7. Baylis, A.B.; Hillman, M.E.D. German Patent, 2155113, 1972, Chem. Abst, 1972, 77, 34174q.
8. Baylis, A.B.; Hillman, M.E.D. German Patent, 2155113, 1972, Chem. Abst, 1972, 77, 34174q.
9. Hoffmann, H.M.R.; Rabe, J. J. Org. Chem., 1985, 50, 3849.
10. Drewes, S.E.; Roos, G.H.P. Tetrahedron, 1988, 44, 4653 and references cited therein
11. 13N: C, 87.63; H. 5.97; N, 6.39; Found C, 87.59; H, 5.95; N, 6.39.
12. The yields of 2e and 2f are lower because of incomplete reaction and presumably considerable formation of the corresponding allyl chlorides
13. 15,16. We have therefore assigned (Z)-stereochemistry to major isomer of 2a. The (Z)-stereochemistry was assigned to 2b-2d by comparing the chemical shift value (δ = ≈ 42) of allylic methylene carbon with that of 2a.
14. 2Cl: C, 62.71; H, 5.26; Found C, 62.67; H, 5.25.
15. Ameer, F.; Drewes, S.E.; Houston-McMillan, M.S.; Kaye, P.T. J. Chem. Soc., Perkin Trans. 1, 1985, 1143.
16. Funabiki, T.; Hosomi, H.; Yoshida, S.; Tarama, K. J. Am. Chem. Soc. 1982, 104, 1560.
17. Basavaiah, D.; Bhavani, A.K.D.; Pandiaraju, S.; Sarma, P.K.S. SYNLETT, 1995, 3, 243.