Synlett 2012; 23(8): 1262-1263
DOI: 10.1055/s-0031-1290961
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© Georg Thieme Verlag Stuttgart · New York

Lead(IV) Acetate

Rammohan R. Yadav
Medicinal Chemistry Division, Indian Institute of Integrative Medicine (IIIM-CSIR), Canal Road, Jammu 180001, India., Email: rammohan.raman@gmail.com
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Publication History

Publication Date:
26 April 2012 (online)

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 ]

 
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