Methylene acetal formation from 1,2- and 1,3-diols using an O, S -acetal, 1,3-dibromo-5,5-dimethylhydantoin, and BHT

Journal of Organic Chemistry

Volumn 78, Issue 7, 2013, Pages 3384-3390

  Maegawa, Tomohiro ^a   Koutani, Yasuyuki ^a   Otake, Kazuki ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIBROMO-5 ,5-DIMETHYLHYDANTOIN; 1 ,3-DIOLS; ACETAL FORMATION; SIDE REACTIONS;

CHEMISTRY;

ORGANIC COMPOUNDS;

1,3 DIBROMO 5,5 DIMETHYLHYDANTOIN; ACETAL DERIVATIVE; BUTYLCRESOL; HYDANTOIN DERIVATIVE; HYDRONIUM ION; METHYLENE ACETAL DERIVATIVE; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; BROMINATION; CHEMICAL REACTION; CYCLIZATION; REACTION TIME; SYNTHESIS; WILLIAMSON REACTION;

ACETALS; ALCOHOLS; BUTYLATED HYDROXYTOLUENE; HYDANTOINS; MOLECULAR STRUCTURE;

EID: 84875963264     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4000256     Document Type: Article

References (38)

1. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4 th ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2006.
2. Fujioka, H.; Senami, K.; Kubo, O.; Yahata, K.; Minamitsuji, Y.; Maegawa, T. Org. Lett. 2009, 11, 5138
3. Fujioka, H.; Senami, K.; Kubo, O.; Yahata, K.; Minamitsuji, Y.; Maegawa, T. Chem. Pharm. Bull. 2010, 58, 426
4. Hough, L.; Jones, J. K. N.; Magson, M. S. J. Chem. Soc. 1952, 1525
5. Bonner, T. G. Methods Carbohydr. Chem. 1963, II, 314
6. Sato, T.; Saito, Y.; Kainosho, M.; Hata, K. Bull. Chem. Soc. Jpn. 1967, 40, 391
7. Burczyk, B. J. Prakt. Chem. 1980, 322, 173
8. Gras, J. L.; Nouguier, R.; Mchich, M. Tetrahedron Lett. 1987, 28, 6601
9. Brusilovskii, Y. E.; Kuznnetsov, V. V. Russ. J. Gen. Chem. 2011, 81, 542
10. Brimacombe, J. S.; Foster, A. B.; Jones, B. D.; Willard, J. J. J. Chem. Soc. C 1967, 2404
11. Kim, K. S.; Szarek, W. A. Synthesis 1978, 48
12. Lipták, A.; Oláh, V. A.; Kerékgyártó, J. Synthesis 1982, 421
13. Norman, D. G.; Reese, C. B.; Serafinowska, H. T. Synthesis 1985, 751
14. Guiso, M.; Procaccio, C.; Fizzano, M. R.; Piccioni, F. Tetrahedron Lett. 1997, 38, 4291
15. Hanessian, S.; Yang-Chung, G.; Lavallee, P.; Pernet, A. G. J. Am. Chem. Soc. 1972, 94, 8929
16. Munavu, R. M. J. Org. Chem. 1980, 45, 3341
17. Bal, B. S.; Pinnick, H. W. J. Org. Chem. 1979, 44, 3727
18. Gu, Z-m.; Zeng, L.; Hang, X-p.; Colman-Saizarbitoria, T.; Huo, M.; MacLaughlin, J. L. J. Org. Chem. 1994, 59, 5162
19. Queiroz, E. F.; Silva, E. L. M.; Roblot, F.; Hocquemiller, R.; Figadére, B. Tetrahedron Lett. 1999, 40, 697
20. Matsuda, F.; Kawasaki, M.; Terashima, S. Tetrahedron Lett. 1985, 26, 4639
21. Angelis, F. D.; Marzi, M.; Minetti, P.; Misiti, D.; Muck, S. J. Org. Chem. 1997, 62, 4159
22. Chu, G.; Zhang, Y.; Li, C.; Zhang, Y. Synthesis 2009, 3828
23. Corey, E. J.; Hase, T. Tetrahedron Lett. 1975, 16, 3267
24. Munavu, R. M.; Szmant, H. H. Tetrahedron Lett. 1975, 16, 4543
25. Karimi, B.; Seradj, H.; Maleki, J. Tetrahedron 2002, 58, 4513
26. 2-Methoxymethylthiopyridine was used for the MOM protection of the hydroxy group in combination with AgOTf: Marcune, B. F.; Karady, S.; Dolling, U.-H.; Novak, T. J. J. Org. Chem. 1999, 64, 2446
27. Hanessian, S. Carbohydr. Res. 1966, 2, 86
28. Failla, D. L.; Hullar, T. L.; Siskin, S. B. Chem. Commun. 1966, 716
29. Gaze, C.; Gilbert, B. C. J. Chem. Soc. Perkin Trans. 2 1977, 1161
30. Giordano, C.; Minisci, F.; Vismara, E.; Levi, S. J. Org. Chem. 1986, 51, 536
31. Zhao, B. X.; Jin, Q. Sci. China Chem. 2011, 54, 1718
32. Yeager, L. J.; Amirsakis, D. G.; Newman, E.; Garrell, R. L. Tetrahedron Lett. 1998, 39, 8409
33. Griffith, J. C.; Jones, K. M.; Picon, S.; Rawling, M. J.; Kariuki, B. M.; Campbell, M.; Tomkinson, N. C. O. J. Am. Chem. Soc. 2010, 132, 14409
34. Grigor'eva, Y. N.; Pinsker, A. O.; Daeva, D. E.; Moiseenkov, M. A. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1991, 40, 2037
35. Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Leahy, E. M.; Salvino, J.; Arison, B.; Cichy, A. M.; Spoors, P. G.; Shakespeare, W. C.; Sprengeler, P. A.; Peter, H.; Smith, A. B., III; Reisine, T.; Raynor, K.; Maechler, L.; Donaldson, C.; Vale, W.; Freidingler, R. M.; Cascieri, M. R.; Strader, C. D. J. Am. Chem. Soc. 1993, 115, 12550
36. Gu, Y.; Karam, A.; JeÌroîme, F.; Barrault, J. Org. Lett. 2007, 9, 3145
37. Guyard, A. L.; Valleix, A.; Rousseau, B.; Cintrat, J. C. J. Labelled Compd. Radiopharm. 2001, 44, 529
38. Landini, D.; Montanari, F.; Rolla, F. Synthesis 1979, 134