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5.3 Product Class 3: Lead Compounds

DOI: 10.1055/sos-SD-005-00610

Moloney, M. G.Science of Synthesis, (20035619.

General Introduction

The chemistry and wider perception of organolead compounds has been dominated by the multiton preparation and use of tetraethyllead as an antiknock petroleum additive for most of the twentieth century. For the synthetic chemist, however, tetraalkyllead derivatives are probably neither the most interesting nor useful, and it is only over the last three decades that certain classes of lead compounds have come to be accepted as valuable synthetic intermediates. Lead(II) salts rarely find application in organic synthesis, but the most well-known lead(IV) salt, lead(IV) acetate, as a result of its high oxidizing potential,[‌1‌] finds application as an oxidant of diverse functional groups; the early studies by Criegee firmly established the utility of lead(IV) acetate in this regard, but inclusion of the details of these applications, however, falls outside the scope of this volume of Science of Synthesis, and the reader is referred to other authoritative reviews of the subject.[‌2‌‌6‌] ­Lead(IV) acetate has, for example, found extensive use in heterocycle synthesis,[‌7‌] and ­sonochemistry has been used to advantage in some cases in the control of selectivity of oxidation processes.[‌8‌] Other lead(IV) salts have emerged as synthetically useful reagents for diverse chemical applications,[‌9‌,‌10‌] and recently the utility of chiral lead(IV) ­carboxylates for oxidative cleavage[‌11‌] and enantioselective aziridinations mediated by lead(IV) acetatechiral ligands[‌12‌] has been recognized.


Me e eeeeee ee eeeee eeeeee, eeee eeeeeee eee eeeeeeeeeeee eeeeeee eeee eeee eeeee: Me8+ eee ee eeeee eeeeee ee 888ee eee Me8+ ee 88ee, eeeeeeee eeee 888ee eee eeee eeeee. Mee eeeeeeeeee eeee Meeeeee eeeeeeeeeeeeeeeee ee eee Me8+ eeeee ee e eeeeee ee eee eeee eeeeee eeeeee. Mee eeeeeeeee eeeeeeeee ee Me8+ ee Me8+ ee 8.88M, eee ee eee eeeeeee ee eee eee eeeeee, eee eeee eeeeeeee eee eeeeeeeeeeeee eeeeee ee eee eeeeeeeeee ee eeee eeeee eeeeee.[‌88‌] Meeeeeee ee ee eee eeeeeeeeee eeeeeeee ee eee eeeeee eeeee (88eee), eeee ee eeeeeee eeeeeeeee eee eeeeeeeeee eeeeeeeeeee.

Mee eeee eeeeee eeeee eeeeeeeeee eeeeeeeee eee eeeee ee eee eeee(MM) eeeeeeeee eeeee; eeeeeeeeee(MM) eeeeeee eee eeeeeeeee eeeeee eeeeeeee eee eeee eeeeeee eeeeeeee eeee ee eeeeeeee eeeeeeeeeeeee ee ee eeeeeeee eeeeeeeee eeeee, eeeee eeee eeeee eeeeee. Me eeeeeeee ee eee eeeeeee eee eee eeeeeeeeee ee eee eeee(MM) eeeeeeeee eeeee eee eeeeeeeee eeeee, eee eee eeee(MM) eeeeeeeee eeeee eee eeeeeeeeee eeeeeeeee, eee eeee eeeeeeeee.[‌88‌] Meeeeeeee ee eeeeeeeeee(MM) eeeeeeeee eeeeeeee ee eee eeee eeeee MMeM8 < M8MeM8 < M8MeM < M8Me, eeeee M ee ee eeeeeeeeeeeeeee eeeeee (e.e., eeeeeeeeeee ee eeeeee) eee eee eeeeeeeeee ee eeeee eeeeeee eeeeeee eeeeeeeeeee. Mee MeM eeee eeeeeeee ee eeeeeeeee eeeee 8.88.8 Å ee eeeeee ee eeeee eeeeeeeee, eee eee eeeeeeeeeeee eeeeee ee eeeeeeeee ee eee eeeeee ee 888 eM·eee8.[‌88‌]

Meeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeee ee eeee eeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeeeee eeee eeeeeeee eeeeee eeeeeeeee. Meeeeeeeeeeeee eeee(MM) eeeeeeeee eeee e eeeeee eeeeeeee MeM eeee, eee eeee eee eeeeeeeeee ee eeeeeeee eeeeeeee.[‌88‌] Meeeeeeee eee eeeee eeee eeee- ee eeeeeeeeeee, eee ee eeee eeee eeeeeeee eeeeeeee eeeeeeeeeeee eeeeeeeeee, eeee eeeeeeeeeeee eeeeeee eeeeeee eeee 8 ee 88; eeeeeee, eee eeee(MM) eee­eeeee eee eeeeeee, eeee eeeeeeeeee eeeeeeeeeeee ee eeeee.[‌88‌] Meeeeeeeeeeeee eeeeeeeee ee eeee eeee eeeeeeeeee eee eee-eeeeeeeeee eeeeee eeeeeee eeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeeeeee eeeeee eee eeee eee eeeeeeeeeee eeeee.[‌88‌]


Meeeeeeeeeeee eeeeeee ee eee eeeeeeeee ee eeeeeeeeee eeeeeeeee eee eeeeeeeee.[‌88‌‌88‌] Meeeeeeeee eeeeeeeee eee eee ee e eeeeee ee eeeeeeeeee, eeeeeeee, ee eeeeeeeeeeee, ee eeeee eeeeeeeee eeeeeeeeeee; eee eeee ee eeeeeeeeee ee eeeeeeeee eeeeeeeeee ee eee eeeeee ee eee eeeeeee ee eee eeee, eee eee eeeeeeee ee eeeeeeeee. Mee eeeeeee, eeeeeeeeeeeeeee eeeeeeeee eee eeeeeee e eeeeee ee eeeeeeeeee;[‌88‌] eeee eeeeeee eeeeeeeeeeeeeeee eee eeeeeeeee, eee ee eee eeeee eeee eeeeeee, ee ee eeeeeeee eeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeee (Meeeee 8) ee eee eeeeeeee ee e eeeeee Meeee eeee, eeee ee eeeeeeee(MM) eeeeeeee (Meeeeeee 8.8.88 eee 8.8.88). Meeeeeeeeeeeeee (Meeeee 8; M8=M8=Me, Me, eMe, Me) eeeee eeee eeeeeeee ee eee eeeee eeeeeee, eee eeeeeeeeeeeeeeeeee (M8=MM=MM8) (Meeeeee 8.8.88) eee eeeeeeeeeeeeeeeeeeee (M8=MMMe) (Meeeeee 8.8.88) eeeeeeee eeee eee eeee eeeeee eeeeeeeeeee eeeeeee. Meeeee eeeeeeeee eeee eeee eee eeeeeeeeeee, eeeeee e eeeeeeeee eeeeee eeeeeeeeeee eeeeeee eeeeee eeeeeeeee. α-Meeeeeeeeeeeeeee eeeeeeeee eeee eeeee eeee eeeeeeeee ee e eeeeee eeeeeeeeeeeeeee eeeeeee, eee eeeeeee ee eeeee eeeeeee ee eee eeeeee ee eee Meeee eeee eeeeeeee. Meee eeeeee eeeeeeeeeeee eeee eeee eee eeeeeeeeeee ee eeeeee Meeee eeee eeeeeeeee (e.e., MeM8/MMMM) eee eee eeeeeeeee ee α,β-eeeee eeeeeee (Meeeeee 8.8.88). Meeeeee-eeee eeeeeeeeee ee eeeeeeeee eee eeeeeee eeee eeeee eeeeeee eee eeeeeeee eeee ee eeeeeee eeeeeee eee eeee eeee eeeeeeee (Meeeee 8); eeee eeeeeeeeee eeeeeeee eeeeeee ee eeeeeeeee eeeeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeee Meeeeeeee ee Meeeeeeeee Meeeeeeee eeee Meeeeeeee

Meeeee 8 Meeeeee-Meee Meeeeeeee Meeeeeee ee Meee[‌88‌]

Mee eeee eeeeee ee MMe eeeee eee eeee eeeeeeeee ee eeeeeee-eeeeeeee eeeeeeeeee eeeeeeeee (Meeeeee 8.8.88).[‌88‌] Meee, α-eeeeeeeeee ee eeeeeeee eeeeeeee eeeeeee eeeee eeeeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeeeee (Meeeee 8).

Meeeee 8 Meeeeee-Meeeeeee Meeeeeeeee Meeeeeee[‌88‌]

Meeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeee ee eeeeeee eeeeee eee eeeeeeeeeeeee ee eeeeee eeeeeeee eeeeeeeee. Mee eeeeeee, eeeeeeeeee(MM) eeeeeeeeeeee (Meeeeee 8.8.8) eee eeeee ee eeeeeee e eeeeeee ee eeeee-eeeeeeee eeeeeeeee, eee eeee eee eeee eeeeeeeeeeee ee eeeeee ee eeeeee eeeee (Meeeeeee[‌88‌,‌88‌,‌88‌,‌88‌] Meeee eeeeeeeee eeeee eeee e eeeeee ee eeeeeeeeee eeeeeeeeeee (Me) ee eeee eee eeeeeee eeeeeee 8 ee eeeeeeeee ee e eee eeeeeeeeeeee ee eeeeeeeeeeeeeeee eeee (Meeeee 8); eeeeeeeee eeeeeeeee ee eeee eee eeeeeeeeeee α-eeeeeeeeeeeee eeeeeeee 8 eee eeee eeeeee eee eee eeeeeee.[‌88‌] Mee eeeeee eeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee eeeeeeeeeeeeee ee eeeee 8 eee eeeeee ee8 eeeeee eeeeeee (M8=eeeee, eeeee) eee eeeeeeee eeeeeee eee eeeeeeeee eeeeeee ee eeeee eeeeeee, eee eeee eeee ee eeeeeeee ee eee eeeeeeeee eeeeeeeeeee eee M8=eeee, eeeee, eee eeeeeee.[‌88‌] Meee ee eeeeeee eeeee eeeee eeeeeeeee ee eeee eee eeeeeeeeeeeeee eeeeeeee eeeeee ee e eeeeeeeeeee eeeeeeeee eeeeeeeeee eee eeeeeeeee eee eeeeeeeee eee eeeeeeee ee eeeeeeee. Meeee ee eee eeeeeeeeeeee eeeeeeee eeee eeeee eeeeeeeee eeeee ee eeeeee eeeeeeee[‌88‌,‌88‌] eeeeeeeee e eeeeeeeee eeeeeeeeeee ee eee eeee eeeeee,[‌88‌,‌88‌] eee eee eeeeeeee eeeeeeeeeeee ee eeeeeeee eeeee eee eeeeeeeeee ee eee eeeeeeeee eeeeeee ee eeee eeee eeeeeeee.[‌88‌] Meeee eeeeeeeee eee eeee eee eee eeee eeeeeeee ee eeee eee eeeeeeeeeee eeeeeeeee eeeeeeeeeee (eeeee ee eeeeee, eeeee, ee eeeeeee eeeeeee) eee eee eeeeee eeeeeeee ee eeeeeeeeeee eeeeee. Meeeeeeeee(MM) eeeeeeeeeeeeeee eeee eeee eeeee ee eeeeeee eeeeeeeeee, eeeeeeeeeee, eee eeeeeeeeeeeee (Meeeee 8; M8=Me, MM=MMM, eee MMM, eeeeeeeeeeee) ee e eeeeeee ee eeeeeeeeeeee eeeeeeeeee, eeeeeeeeee eeee eeeeee eeeeeeeeeeee eeee ee eeeeee eeeeeeee, eeeeeeee, eeeeeee, eee β-eeeeeeeeee eeeeeeeee, eee eeee eeee eeeeeeeeeeeeeeeeee, e.e. eeeeee ee eeeee. Mee eeeeeeeeee ee eeeeeee ee eeee eeeeeeeeee-eeeeeeee eeeeeeeee eee eeee eeeeeeeeeeee, eeeeeeeeeeee ee eee eeeeeee ee eeeeeeeeeeeeeeee[‌88‌‌88‌] eee eeeeeeeeeeeeee,[‌88‌,‌88‌] eee eeeeeeeeeee eeee eeeeeeeeeeee eee ee eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeee.[‌88‌] Meeeeee, ee ee eeeee eeee eeeee eeeeeeeeeeeeee eeee eeeeeeeeeee ee eeeeeeeeee eeeeeeeee eeeeee eeee eeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeee, eee eeee eee eeeeeeee eee eeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee.

Meeeee 8 Meeeeeee Meeeeeeee ee Meeeeeeeee Meeeeeeeeeeeeee[‌88‌]

Meeee eeeeeeeee eee/ee eeeeee eeeeeeeee, eeeeeeeeee(MM) eeeeeeeeeee (Meeeeee eee ee eeeeeeeeeee ee eee eeeeeee[‌88‌] ee eeeeeeee[‌88‌] ee eeeeee eeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeee eee eeeeeeeee (Meeeee 8) ee eeeeeee (Meeeee 8). Meee eee ee eeeee eeeeeee eeee eeeeeee ee eeee eeeeeeeeeeeee eeeeeee (Meeeee 8),[‌88‌] eeeeeeeeeeeeeee ee eeee eeeeeee, eeeeeee, ee eeeeeee (Meeeee 8),[‌88‌] eeeeeeeeeeeee[‌88‌] ee eeeeeeeeeee eeeeeeee eeeee[‌88‌] ee eeee eeeeeeeeeeeee eeeeeee ee eeeeeee (Meeeeee 8 eee 88), eee eeeeeeee eeeeeee ee eeee eeeeeeeeeeeee eeeeeee (Meeeee 88).[‌88‌] Me eeeee eeeeeeeee, eeee eee eeeeee ee eee eeeeeeee eeee eeeeeeeeeeee eee eeeeeeee.

Meeeee 8 Meeeeeeeee Meeee Meeeeeeee Meeeeeeeeeee Meeeeeeee[‌88‌]

Meeeee 8 Meeeeeeee(8)-Meeeeeeee Meeeeeeeeeeee Meeeeeee Meeeeeeee[‌88‌]

Meeeee 8 Meeeeeeee(8)-Meeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeeeeee eeee Meeeeee[‌88‌]

Meeeee 8 Meeeeeeee(8)-Meeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeeeeee eeee ­Meeeeeeeeeeeeee[‌88‌]

Meeeee 8 Meeeeeeee(8)-Meeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeeeeee eeee ­Meeeeeeeeeeee[‌88‌]

Meeeee 88 Meeeeeeee(8)-Meeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeeeeee eeee Meeeeeeeeee Meeeeeee Meeee[‌88‌]

Meeeee 88 Meeeeeeee(8)-Meeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeeeeee eeee Meeeeeee ­Meeeeee[‌88‌]

Meeee eeeeee(MM) eeeeeeeee, eeeeeeee eeeeeeeeeee eeeee eeee e eeeeeee ee eeeee eeeeee, eeeeeeee, ee eeeeeeeeee eeeeee ee eeee eee eeeeeeee eeee M-eeeeeeeee (Meeeeee, Meeeee 88).[‌88‌] Mee eeeeeeee ee eeeeee eeee eeeeeeeeeeeeee eeeeeeeee ee eeee eeeeee, eee eee eeee eeeeeeee eeee eeee eeeeeeeee eeeee eeeeeeeee(8) eeeeeeeee (Meeeeee 8.8.88) ee eeee eeeeeee (Meeeee 88),[‌88‌] eee eeee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee eeeee eeeeeee eeeeeeeee ee eeee eee eeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeee eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeee-Meeeeeeee Meeeeeee ee Meeeeeeeee Meeeeeeeeee eeee Meeeee[‌88‌]

Meeeee 88 Meeeeeeee(8)-Meeeeeeee Meeeeeee ee Meeeeeeeeeeeeee Meeeeeeee eeee Meee Meeeeeeee[‌88‌]

Meeeee 88 Meeeeee-Meeeeeeee Meeeeeee ee Meeeeeeeeeeeeee Meeeeeeee eeee ­α,β-Meeeeeeeeee Meeeeeee Meeeeeeee[‌88‌]

Meeeeeeeee eeeeeeee (Meeeeee 8.8.8) eee eeeeeee ee eeeeeeee eeeee, eeeee, eee eeee eeeeeee, eee eeee eee eeeee eee ee eeeeeeeee eeeeeeeee eee ee eeeee eeeeeeeeee ee eeeeeeeeeee eee eeee eeeeeeeeee, ee eeeee eeeeeeee ee eee eeee eeeeeee eeeeeeeee eeeeeeeeeee eeeeeeee. Meee eeee eee eeeeeeeeeee ee eeeeeeeeeee eeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeee eeeeeee (Meeeee 88),[‌88‌‌88‌] eee eeeee eeeeeeeee, eee, eee eeee eeeeee eeee eeee eee eeeeeee eeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeee Meeeeeeee ee Meeeeeeeeeeee Meeeeeee[‌88‌‌88‌]


Me eee MM eeeeeeee, MeM eeeeeeeeee eeeeeeeeee eeeeeee eeeee ee 888888ee8, eee MeM ee eee eeeee 88888888ee8.

Mee ee eee eeeeeeee ee eeee ee MMM eeeeee: 888Me, eeee e eeee M=8/8, eee e eeeeeee eeeeeeeee ee 88.8% eee eeeeeeeee eeeeeeeee ee 88.8888Me, eeeeee ee e eeeeeeeeeee ee 88.8 eeeeeeee ee 88M, eee eeeeee ee e eeeeee eeeeeeeeee eeeeeee eee MMM eeeeeeeeeeeee.[‌88‌‌88‌] Meeeeeeeee eeeeeeee eeeee eeeeee eee eeeeeeeee ee eeeeeeeeeeeee, eeeeeee, eee eeeeeeeeeee, eeee eeeeee eeeeeeeee ee eee eeeee 8888 ee +888eee. Meeeeeeeee ee eeee eee eeeeeeeeee eeeeeeee eeeeeeeee, ee ee eeeeeeeee eeeee eeee 8MMeM > 8MMeM eee eeee eee eeeeeeeeee eeeeeeee eeeeeeeee 8MMeM >> 8MMeM > 8MMeM > 8MMeM. Meeeeeeeee eee eeeeeeee ee eee 8M eee 88M MMM eeeeeee ee eeeeeeeeee eeeeeeeee, ee 88.8% eeeeeeeee ee eee eeeeeeee eee eeeeeeeeeeeee eeeeeeee eeeee eee eeeeeee eeeee. Mee eeeeeeeeeee ee eeeee-eeeee MMM eeeeeeeeee ee eeeeeeeeee eeeeeeeee eee eeee eeeeeeee.[‌88‌]

Meeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee ee eeee eeeeeeeeeeeee eeeeeeee ee eeee eeeeeeeee, eeee eee eeeeeeee eeeee ee eeeee eeeeeeeeee eee eeeeeeee eeeeeeeee, eee eeee eeeeeeeee eee ee eeeee eeeeeeeeeeeee eeeeeeeeee. Mee eeeeeeee ee eeee ee eeeeeee ee eee eeeeeeeeeeeeee eeeeeeee eeeeeeeeeeee eeeeeee [eeeeeeee eeeeeeee eeeeeeeee: 888Me (8.8%), 888Me (88.8%), 888Me (88.8%), 888Me (88.8%)] eeeeeeee eee eeeeee eee ee eeeeeee eeee eeee. Meee eeeeeeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeee, ee eeeeeeee, eee eeee eeeeeeee eeeeee eeeeeeee eeee eee eeeeee ee MMMMM eeeeeeeeee.[‌88‌]


Mee eeeeeeee ee eeee ee ee eeeee eeeeeee, eeeeeee eeeeeeeeeee eeee eee eee ee eeeeeeee eeee eee eeeee eeeeeeeeeeee. Mee eeeeeeeee ee eeeeeeee eee eeee-eeeee eeeeeeee eee eeeeeeeee eeeeeeeeeeee eee eeee eeeee[‌88‌,‌88‌] eee ee ee eeee eeeeeeeeee ee eeee eeeee eeeeeeee eeee eeeeee; eeeeeeeeee eee eee eeeeeee eeeeee ee eeeeeeee ee eeeeeeeee eee eeee.[‌88‌] Meeeee eeee eee eeeeeeeeeee eeee eeeeeeeeeee eeeeee ee eeee-eeeeeeeeee eeeeeeeee eee eeee eeee eee eeeeee ee eeee ee eee eeeee eeeeeee.[‌88‌,‌88‌]

Meeeeeeeeeee ee eee Meeeeee Meeee Meee Meeeeeeee

Mee eeeeeeee eeeeeeeee ee Meeeeee 8.8 (Meee Meeeeeeee) ee eeeeeeee eeeeeeeee ee eee eeeeeeeeeeeeee eeeeeeeeee ee Meeeeee ee Meeeeeeee: eee eeeeeee eeeee eeeeee eeeeeeeeee ee eeeee eeeeeee eeeeeeee eee eeeee eeeeeeee ee eeeeeeee. Meee, eeeeeee, eeee eeee(MM) eeeeeee (eeee eeeee), eeeeeee eee eeeeeeeeeeee eeeeeeeee eeeeeee, ee eee eeeeeeee eeeee ee ee eee ee eeeeeeeeeeeeee eeeeeeee. Meee, eeeee eeeeeee eee eee eeeeeeeee eee eeeeeeeeeeeeeeee ee e eeeeee ee eeeeeeeeee eeeeeeeee ee eee eeeeeeeeee eee eeeeeee, eeee eeeeeee eeeee eeeeee eeeee eeee eeee ee eeeeeeeeeeeee eeee, eee eeeeeeeeee ee eee eeeeeeeee eeeee ee eeeee eeeeeeee ee eeee eeee eeeeeeeee. Meeeeeeeeee, ee eeeeeee eee eeee eeee ee eeee e eeeeeeeee eeeeeeee ee eee eeeeeeeeeee eee eeeeeeeee eeeee ee eeee eeeee ee eeeeeeeee. Mee eeeeeeeee ee eeee eeeeeee ee eeeeeeee ee eeee eee eeeeee ee eeeeeeee ee eeeeeeeeee eeeeeeeee ee ee eeeeeeeee eeeeee, ee eeee ee ee eeeeeeee eeeee eeee ee eeeeeeee eeeeeeeee eee eeeeeeeeeee eeeee.