Selective ortho-cleavage of methoxymethyl- and 4-methoxybenzyl ethers

Tetrahedron Letters

Volumn 45, Issue 13, 2004, Pages 2739-2742

  Keith, John M ^a  

^a LLC   (United States)

Author keywords

Iodine; Methanol; MOM; PMB; Selective cleavage; Solvolysis

Indexed keywords

4 METHOXYBENZYL ETHER; CHLORIDE; ETHER DERIVATIVE; METHOXYMETHYL ETHER; METHYL GROUP; UNCLASSIFIED DRUG;

CATALYSIS; CATALYST; CHEMICAL REACTION; CONFERENCE PAPER; OXIDATION;

EID: 1542298840     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.039     Document Type: Conference Paper

References (18)

1. Arnaudinaud V., Nay B., Nuhrich A., Deffieux G., Merillon J.-M., Monti J.-P., Vercauteren J. Tetrahedron Lett. 42:2001;1279-1281.
2. Vaino A.R., Szarek W.A. Chem. Commun. 1996;2351-2352.
3. Vaino A.R., Szarek W.A. Synlett. 1995;1157-1158.
4. Szarek W.A., Zamojski A., Tiwari K.N., Ison E.R. Tetrahedron Lett. 27:1986;3827-3830.
5. Sampath Kumar H.M., Subba Reddy B.V., Jagan Reddy E., Yadav J.S. Chem. Lett. 1999;857-858.
6. Ramasamy K.S., Bandaru R., Averett D. Synth. Commun. 29:1999;2881-2894.
7. Wahlstrom J.L., Ronald R.C. J. Org. Chem. 63:1998;6021-6022.
8. Ramalinga K., Vijayalakshmi P., Kaimal T.N.B. Tetrahedron Lett. 43:2002;879-882.
9. Lipshutz B.H., Keith J. Tetrahedron Lett. 39:1998;2495-2498.
10. Cruickshank F.R., Benson S.W. J. Phys. Chem. 73:1969;733-737.
11. 4, filtered and evaporated to dryness to give the crude product. The products can be purified chromatographically or by recrystallization (acids).
12. 1H NMR. NOE analysis further confirmed the assigned structures.
13. Ohira S., Fukamachi N., Nakagawa O., Yamada M., Nozaki H., Iinuma M. Chem. Lett. 2000;464-465.
14. Tatsuta K., Nakano S., Narazaki F., Nakamura Y. Tetrahedron Lett. 42:2001;7625-7628.
15. Ramesh C., Ravindranath N., Das B. J. Org. Chem. 68:2003;7101-7103.
16. 2, undergoes reduction to Pd(0) (palladium mirror was evident) leading to the generation of HCl.
17. Reaction rates can be improved by increasing the catalyst loading, but for the sake of this study, were kept constant to afford meaningful comparisons between catalysts.
18. Chen M.-Y., Lee A.S.-Y. J. Org. Chem. 67:2002;1384-1387.