Lead tetraacetate reactions

In most cases the carbon radical formed in the hydrogen abstraction step 2 will react with the radical R formed in the homolysis of the X—R bond. However, a cage reaction does not seem to be involved in this step. This has been established in the nitrite photolysis and probably applies to hypohalites as well. In the lead tetraacetate reaction, the steps following the oxyradical formation leading to tetrahydrofuran derivatives are less clear. 

K. Heusler, unpublished results. 62a. This statement does not apply to the reaction of 6/S-hydroxy steroids, as both the hypoiodite as well as the lead tetraacetate reactions furnish the same 6/S, 19-oxido compounds in high yields. 

Lactone formation by hypoiodite functionalization, 251 Lead tetraacetate, 147, 150 Lead tetraacetate reactions, 207, 239, 240, 281... 

The lead tetraacetate reaction between jV-aminophthalimide and (E) stilbene was first described by Rees,5 and the hydrazinolysis of the addition product by Carpino.6 The procedures described here incorporate their methods, with improvements. The dimesylate-hydrazine reaction was first described by Paulsen7 in the carbohydrate series. 

Since in the reaction of 20a- and 200-alcohols with lead tetraacetate somewhat similar relative reactivity has been reoorded (L. Velluz, G. Muller, R. Bardoneschi, and A. Poittevin, Cornpt. Rend., 1960, 725), this strongly suggests that the conformational requirements in the transition state of the lead tetraacetate reaction are comparable with those of the Barton reaction. Also see ref. 6 and G. Cainelli, B. Kamber, J. Keller, M. Lj. Mihailovic, D. Arigoni, and O. Jeger, Helv. Chim. Acta, 44, 518 (1961). 

Figure 3 - Lead tetraacetate reaction with styrene...

Lead tetraacetate Reactions via aminonitrenes Aziridines from ethylene derivs. 

It is well known that polyamides and polyether chains are cleaved in hydrolytic conditions. Polymers containing OH in the a position, such as cellulose or poly(vinyl alcohol), can be cleaved by an oxidizer such as periodic acid or lead tetraacetate (reaction 25). The cleavage is very specific, as explained by its mechanism in Scheme 30, and this reaction allows the determination of head to head structures in PVA. 

Lead tetraacetate Reaction of oximes with lead tetraacetate fran5-Bis(l,l-acetoxynitroso compounds) from aldoximes... 

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