S-Thioacyldithiophosphates in the Synthesis of Thiohydroxamic Acids and O-Thioacylhydroxylamines

Abstract

S-Thioacyldithiophosphates proved to be excellent thioacylating agents. They are easily available from carboxylic acids. Due to their low reactivity towards oxygen nucleophiles and high reactivity towards nitrogen ones they found application in the synthesis of thiohydroxamic acids directly from hydroxylamines without protection on the hydroxy group. However, in cases of steric hindrance O-thioacyl hydroxylamines are formed and can be isolated with high yield.

Key words

thiohydroxamic acids - hydroxylamines - acylations - phosphates - chemoselectivity

References

• 2 Scheithauer S. Mayer R. In Thio- and Dithiocarboxylic Acids and Their Derivatives   Vol. 4:  Senning A. Thieme; Stuttgart: 1979. 
• 3 Cherkasov RA. Kutyriev GA. Pudovik AN. Tetrahedron  1985,  41:  2567 
• 4 Cava MP. Levinson MI. Tetrahedron  1985,  41:  5061 
• 5 Ito Y. Umino K. Sekguchi T. Miyagishima T. Egawa Y. J. Antibiot.  1971,  24:  131 
• 6 Black DStC. Ooi KL. Aust. J. Chem.  1988,  41:  47 
• 7 Przychodzen W. Chimiak A. Phosphorus, Sulfur, Silicon Relat. Elem.  1998,  143:  77 
• 8 Prabhakar S. Lobo AM. Santos MA. Rzepa HS. Synthesis  1984,  829 
• 9 Zacharie B. Sauve G. Penney C. Tetrahedron  1993,  49:  10489 
• 10 Hoeg-Jensen T. Olsen C. Holm A. J. Org. Chem.  1994,  59:  1257 
• 11 Katritzky AR. Moutou J. Yang Z. Synthesis  1995,  1497 
• 12 Kato S. Hattori E. Sato H. Mizuta M. Ishida M. Z. Naturforsch. B  1981,  86:  783 
• 13 Kato S. Shibahashi H. Katada T. Tagaki T. Noda I. Mizuta M. Goto M. Lieb. Ann. Chem.  1982,  1229 
• 14 Doszczak L. Rachon J. J. Chem. Soc. Chem. Commun.  2000,  2093 
• 15 Boche G. Bosold F. Schroder S. Angew. Chem. Int. Ed. Engl.  1988,  27:  973 
• 16 Bitner S. Tetrahedron Lett.  1965,  95 
• 17 Prabhakar S. Lobo AM. Marques MM. Tetrahedron Lett.  1982,  23:  1391 
• 18 Lobo AM. Marques MM. Prabhakar S. Rzepa HS. J. Org. Chem.  1987,  52:  2925 
• 19 Ferreira LM. Lobo AM. Prabhakar S. Marcelo-Curto MJ. Rzepa HS. Yi MY. J. Chem. Soc., Chem. Commun.  1991,  1127 
• 20 Lobo AM. Marques MM. Prabhakar S. Rzepa HS. J. Chem. Soc., Chem. Commun.  1985,  1113 
• 21 Ferreira LM. Lobo AM. Prabhakar S. Teixeira AC. Tetrahedron  1999,  55:  3541 
• 22 Murray KS. Newman PJ. Gatehouse BM. Taylor D. Aust. J. Chem.  1978,  31:  983 

1

Chimiak, A.; Przychodzen, W.; Rachon, J. Heteroatom Chem., 2002, 13, 169.