Aldol Condensation of Cycloalkanones with Aromatic Aldehydes Catalysed with TiCl3(SO3CF3)
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N. Iranpoor, B. Zeynizadeh and A. Aghapour
Abstract
Efficient cross-aldol condensation of cyclopentanone, cyclohexanone and 1-indanone with various aromatic aldehydes is catalysed with TiCl3(SO3CF3) at room temperature in excellent yields.
References
J. Deli, T. Lorand, D. Szabo and A. Foldesi, Pharmazie, 1984, 39, 539 CAS.
(a) A. T. Nielsen and W. Houlihan, J. Org. React., 1968, 16, 1 Search PubMed;
(b) R. J. Murray and N. H. Cromwell, J. Org. Chem., 1976, 41, 3540 CrossRefCAS;
(c) J. V. Sinisterra and A. Garcia-Raso, Synthesis, 1984, 502 CrossRef;
(d) R. L. Reeves,
Chemistry of Carbonyl Group, ed.
S. Patai,
Wiley-Interscience,
New York,
1966,
p. 580 Search PubMed.
M. Iwata and S. Emoto, Bull. Chem. Soc. Jpn., 1976, 49, 1369 CAS.
K. Irie and K. I. Watanabe, Bull. Chem. Soc. Jpn, 1980, 53, 1366 CAS.
R. G. Kelleher, M. A. McKervey and P. J. Vibuljan, J. Chem. Soc., Chem. Commun., 1980, 486 RSC.
K. I. Watanabe and A. Imazawa, Bull. Chem. Soc. Jpn., 1982, 55, 3208 CAS.
C. Chuit, R. T. P. Corriu and C. Reye, Synthesis, 1983, 294 CrossRefCAS; R. Mahrwald and H. Schick, Synthesis, 1990, 593.
T. Nakamo, S. Irifune, S. Umano, A. Inada, Y. Ishii and M. Ogawa, J. Org. Chem., 1987, 52, 2239 CrossRef.
M. Zeheng, L. Wang, J. Shao and Q. Zhong, Synth. Commun., 1997, 27, 351 CrossRefCAS.
N. Iranpoor and F. Kazemi, Tetrahedron, 1998, 54, 9475 CrossRefCAS.
N. Iranpoor and B. Zeynizadeh, J. Chem. Res., 1998, 466 (Synlett, 1998, 1079) RSC.
R. Noftle and G. H. Cady, Inorg. Chem., 1966, 5, 2182 CrossRefCAS.
(a) C. E. Garlan and E. Emmet Reid, J. Am. Chem. Soc., 1925, 47, 2335;
(b) A. Maccioni and E. Marongiu, Ann. Chim. (Rome), 1958, 48, 557 (Chem. Abstr., 1959, 53, 5227i) CAS;
(c) N. P. Buu-Hoi and N. D. Xoung, Bull. Soc. Chim. Fr., 1958, 758 CAS.
A. C. Huitric and W. D. Kulmler, J. Am. Chem. Soc., 1956, 78, 614 CrossRefCAS.
D. N. Kevill, E. D. Weiler and N. H. Cromwell, J. Org. Chem., 1964, 29, 1276.
D. N. Kevill, E. D. Weiler and N. H. Cromwell, J. Am. Chem. Soc., 1966, 88, 4489 CrossRefCAS.
N. P. Buu-Hoi and N. D. Xoung, J. Chem. Soc., 1952, 2225 RSC.
G. A. Coppens, M. Coppens, D. N. Kevill and N. H. Cromwell, J. Org. Chem., 1963, 28, 3267 CAS.
R. Huisgen and W. Rapp, Chem. Ber., 1952, 85, 826 CAS.
C. R. Harrison, Tetrahedron Lett., 1987, 28, 4135 CrossRefCAS.
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