Benzyl trityl ether and DDQ as new tritylating reagents

Synlett

Volumn , Issue 7, 1998, Pages 757-760

  Oikawa, Masato ^a   Yoshizaki, Hiroaki ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013006999     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1777     Document Type: Article

References (16)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley and Sons, Inc.: New York, 1991.
2. Bessodes, M; Komiotis, D.; Antonakis, K. Tetrahedron Lett. 1986, 27, 579-580.
3. Malanga, C. Chem. Ind. (London), 1987, 856-857.
4. Chaundhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 95-98.
5. Reddy, M. P.; Rampal, J. B.; Beaucage, S. L. Tetrahedron Lett. 1987, 28, 23-26.
6. Hernandez, O.; Chaudhary, S. K.; Cox, R. H.; Porter, J. Tetrahedron Lett. 1981, 22, 1491-1494.
7. Murata, S.; Noyori, R. Tetrahedron Lett. 1981, 22, 2107-2108.
8. 4. After evaporation of the solvent, the residue was purified by silica-gel flash chromatography to yield a Tr ether.
9. 22O: C, 89.11; H, 6.33. found: C, 89.12; H, 6.30.
10. Jones, P. G.; Dölle, A.; Kirby, A. J.; Parker, J. K. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1989, C45, 234-237.
11. tert-Alkyl benzyl ethers are oxidatively decomposed by DDQ. For example, see: Oikawa, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1985, 26, 1541-1544.
12. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
13. The calculation was performed using Spartan software. Spartan, version 4.0; Wavefunction, Inc., 18401 Von Karman Ave., Ste. 370, Irvine, CA 92612 USA, 1993-1995.
14. 1.
15. The molecule III is not at an energy minimum of the complex of benzaldehyde and the Tr cation at AM1 level.
16. Acidic 2,3-dichloro-5,6-dicyanohydroquinone generated by reduction of DDQ is reported to be insoluble in DCM, see: Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885-888.