Mechanism
Cis-diols are cleaved more readily compared to trans diols (Scheme 6). Different mechanistic interpretations are thus proposed for the two processes (Scheme 7):
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Scheme 6 |
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Scheme 7 |
In addition, the reaction conditions can be used for the oxidative cleavage of the compounds such as β-amino alcohols, 1,2-diamines, α-hydroxy carbonyl and 1,2-dicarbonyl to give similar results (Scheme 8).
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Scheme 8 |
1.6.2.3 Cyclization of Saturated Alcohols
The alcohols having δ hydrogen undergoes cyclization in presence of LTA via a radical pathway to give
tetrahydrofuran
along with low yield of tetrahydropyrans (Scheme 9).
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Scheme 9 |