Subscribe to RSS
DOI: 10.1055/s-0031-1290961
Lead(IV) Acetate
Publication History
Publication Date:
26 April 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201208/lookinside/thumbnails/10.1055-s-0031-1290961-1.jpg)
Introduction
Lead acetate or lead tetraacetate (LTA) is a versatile oxidizing agent, which has been widely used in the organic synthesis and as an excellent reagent for the introduction of lead into organolead compounds. It is hygroscopic and toxic in nature. It has several applications in organic synthesis viz. synthesis of fullerenyl esters,[ 1 ] formation of spirocyclic tetrahydrofuran derivatives,[ 2 ] diastereoselective aziridination of enones,[ 3 ] C–N bond formation[ 4 ] and several others. Very interesting multistage heterodomino transformation,[ 5 ] oxidative fragmentation of homoallylic alcohols,[ 6 ] and an oxidative cleavage of allyl alcohols induced by the O3/Pb(OAc)4,[ 7 ] oxidative decyclization in the synthesis of 6-hydroxycarvone derivatives [ 8 ] have been more recently reported.
LTA can be prepared by slowly adding red lead oxide (Pb3O4) to a mixture of acetic acid and acetic anhydride at 60–80 °C. This mixture is to be cooled followed by filtration and finally recrystallization of the obtained solid residue from acetic acid to yield white needles of LTA.[ 9 ]
-
References
-
1 Li F.-B, Liu T.-X, Huang Y.-S, Wang G.-W. J. Org. Chem. 2009; 74: 7743
- 2 Khan FA, Sudheer Ch, Soma L. Chem. Commun. 2007; 4239
- 3 Duan P.-W, Chiu C.-U, Lee W.-D, Pan LS, Venkatesham U, Tzeng Z.-H, Chen K. Tetrahedron: Asymmetry 2008; 19: 682
- 4 Yang KS, Chen K. Org. Lett. 2002; 4: 1107
- 5 Finet L, Candela LenaJ. I, Kaouchi T, Birlirakis N, Arseniyadis S. Chem. Eur. J. 2003; 9: 3813
- 6 Preite MD, Cueller MA. Chem. Commun. 2004; 1970
- 7 Alvarez-Manzaneda EJ, Chahboun R, Cano MJ, Torres EC, Alvarez E, Alvarez-Manzaneda R, Haidour A, Lopez JM. R. Tetrahedron Lett. 2006; 47: 6619
- 8 Valeev RF, Bikzhanov RF, Selezneva NK, Gimalova FA, Miftakhov MS. Russ. J. Org. Chem. 2011; 47: 1287
- 9 Brauer G. Handbook of Preparative Inorganic Chemistry I. 2nd ed; 1963: 767-769
- 10 Kotali A, Nasiopoulu DA, Harris PA, Helliwell M, Joule JA. Tetrahedron 2012; 68: 761
- 11 Kubo Y, Watanabe K, Nishiyabu R, Hata R, Murakami A, Shoda T, Ota H. Org. Lett. 2011; 13: 4574
- 12 Hussain HH, Babic G, Durst T, Wright JS, Flueraru M, Chichurau A, Chepelev LL. J. Org. Chem. 2003; 68: 7023
- 13a Coseri S, Mendenhall GD, Ingold KU. J. Org. Chem. 2005; 70: 4629
- 13b Coseri S. J. Phys. Org. Chem. 2009; 22: 397
- 14 Fischer DF, Sarpong R. J. Am. Chem. Soc. 2010; 132: 5926
- 15 Fernandez EM. S, Lena JI. C, Altinel E, Birlirakis N, Barrero AF, Arseniyadis S. Tetrahedron: Asymmetry 2003; 14: 2277
- 16a Alvarez-Manzaneda E, Chahboun R, Alvarez E, Alvarez-Manzaneda R, Munoz PE, Jimenez F, Bouanou H. Tetrahedron Lett. 2011; 52: 4017
- 16b Alvarez-Manzaneda E, Chahboun R, Alvarez E, Alvarez-Manzaneda R, Munoz PE, Jimenez F, Bouanou H. Tetrahedron 2011; 67: 8910
- 17 Kim JJ, Park YD, Cho SD, Kim HK, Chung HA, Lee SG, Falck JR, Yoon YJ. Tetrahedron Lett. 2004; 45: 8781