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 <A NAME="RP00502SS-1">1 </A>
Chimiak, A.; Przychodzen, W.; Rachon, J. Heteroatom Chem. , 2002 , 13, 169.
<A NAME="RP00502SS-2">2 </A>
Scheithauer S.
Mayer R. In
Thio- and Dithiocarboxylic Acids and Their Derivatives
Vol. 4:
Senning A.
Thieme;
Stuttgart:
1979.
<A NAME="RP00502SS-3">3 </A>
Cherkasov RA.
Kutyriev GA.
Pudovik AN.
Tetrahedron
1985,
41:
2567
<A NAME="RP00502SS-4">4 </A>
Cava MP.
Levinson MI.
Tetrahedron
1985,
41:
5061
<A NAME="RP00502SS-5">5 </A>
Ito Y.
Umino K.
Sekguchi T.
Miyagishima T.
Egawa Y.
J. Antibiot.
1971,
24:
131
<A NAME="RP00502SS-6">6 </A>
Black DStC.
Ooi KL.
Aust. J. Chem.
1988,
41:
47
<A NAME="RP00502SS-7">7 </A>
Przychodzen W.
Chimiak A.
Phosphorus, Sulfur, Silicon Relat. Elem.
1998,
143:
77
<A NAME="RP00502SS-8">8 </A>
Prabhakar S.
Lobo AM.
Santos MA.
Rzepa HS.
Synthesis
1984,
829
<A NAME="RP00502SS-9">9 </A>
Zacharie B.
Sauve G.
Penney C.
Tetrahedron
1993,
49:
10489
<A NAME="RP00502SS-10">10 </A>
Hoeg-Jensen T.
Olsen C.
Holm A.
J. Org. Chem.
1994,
59:
1257
<A NAME="RP00502SS-11">11 </A>
Katritzky AR.
Moutou J.
Yang Z.
Synthesis
1995,
1497
<A NAME="RP00502SS-12">12 </A>
Kato S.
Hattori E.
Sato H.
Mizuta M.
Ishida M.
Z. Naturforsch. B
1981,
86:
783
<A NAME="RP00502SS-13">13 </A>
Kato S.
Shibahashi H.
Katada T.
Tagaki T.
Noda I.
Mizuta M.
Goto M.
Lieb. Ann. Chem.
1982,
1229
<A NAME="RP00502SS-14">14 </A>
Doszczak L.
Rachon
J.
J. Chem. Soc. Chem. Commun.
2000,
2093
<A NAME="RP00502SS-15">15 </A>
Boche G.
Bosold F.
Schroder S.
Angew. Chem. Int. Ed. Engl.
1988,
27:
973
<A NAME="RP00502SS-16">16 </A>
Bitner S.
Tetrahedron Lett.
1965,
95
<A NAME="RP00502SS-17">17 </A>
Prabhakar S.
Lobo AM.
Marques MM.
Tetrahedron Lett.
1982,
23:
1391
<A NAME="RP00502SS-18">18 </A>
Lobo AM.
Marques MM.
Prabhakar S.
Rzepa HS.
J. Org. Chem.
1987,
52:
2925
<A NAME="RP00502SS-19">19 </A>
Ferreira LM.
Lobo AM.
Prabhakar S.
Marcelo-Curto MJ.
Rzepa HS.
Yi MY.
J. Chem. Soc., Chem. Commun.
1991,
1127
<A NAME="RP00502SS-20">20 </A>
Lobo AM.
Marques MM.
Prabhakar S.
Rzepa HS.
J. Chem. Soc., Chem. Commun.
1985,
1113
<A NAME="RP00502SS-21">21 </A>
Ferreira LM.
Lobo AM.
Prabhakar S.
Teixeira AC.
Tetrahedron
1999,
55:
3541
<A NAME="RP00502SS-22">22 </A>
Murray KS.
Newman PJ.
Gatehouse BM.
Taylor D.
Aust. J. Chem.
1978,
31:
983
