Thermal decomposition of ozonides. A complementary method to the Baeyer–Villiger oxidation of hindered ketones

1979 ◽  
Vol 57 (24) ◽  
pp. 3272-3277 ◽  
Author(s):  
Richard Lapalme ◽  
H.-Jürg Borschberg ◽  
Pierre Soucy ◽  
Pierre Deslongchamps
Keyword(s):  
Thermal Decomposition ◽  
Carboxylic Acid ◽  
Vinyl Acetate ◽  
Mixed Anhydride ◽  
Complementary Method ◽  
Villiger Oxidation

Treatment of vinyl acetate with ozone yields the mixed anhydride of acetic and formic acids and formaldehyde oxide. The formaldehyde oxide can be trapped by reaction with ketones yielding the corresponding ozonides. Thermal decomposition of these ozonides gave the corresponding lactone and (or) the corresponding olefin carboxylic acid. The ozonides were also prepared by the ozonolysis of the corresponding olefins.

Synthesis of Linear Steroid Oligoesters Based on Etienic Acid

2002 ◽  
Vol 67 (11) ◽  
pp. 1709-1718 ◽  
Author(s):  
Miroslav Reschel ◽  
Miloš Buděšínský ◽  
Ivan Černý ◽  
Vladimír Pouzar ◽  
Pavel Drašar
Keyword(s):  
Carboxylic Acid ◽  
Nmr Spectra ◽  
Mixed Anhydride

Linear oligoesters based on etienic acid (3β-hydroxyandrost-5-ene-17β-carboxylic acid) containing 2-4 steroid units were prepared employing mixed anhydride esterification. NMR spectra of the oligomeric steroids have been fully assigned.

scholarly journals “Exhaustive” Baeyer-Villiger Oxidation of Poly(Methyl Vinyl Ketone) and Its Copolymers

2021 ◽  
Author(s):  
Pengfei Ma ◽  
Christopher M. Plummer ◽  
Luo Wenjun ◽  
Jiyan Pang ◽  
Yongming Chen ◽  
...  
Keyword(s):  
Vinyl Acetate ◽  
Chain Scission ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
One Pot ◽  
Methyl Vinyl ◽  
Modification Procedure ◽  
Post Modification ◽  
User Friendly ◽  
Villiger Oxidation

Poly(vinyl acetate) and its copolymers represent an important class of commodity polymers. However, the preparation of copolymers of vinyl acetate (VAc) and more activated monomers (MAMs) <i>via</i> copolymerization is greatly restricted due to their disparate reactivities. Issues relating to reactivity ratios remain a fundamental challenge in copolymerization. Herein, we describe a post-polymerization modification approach using poly(methyl vinyl ketone-<i>co</i>-MAM)s as substrates to access synthetically challenging poly(VAc-<i>co</i>-MAM)s. Although the direct translations of existing small-molecule Baeyer-Villiger (BV) protocols into a post-polymerization modification method failed, a mechanism-guided multi-parameter optimization on polymer substrates disclosed a set of unique “exhaustive” BV protocols which enabled a nearly quantitative functionalization without obvious chain scission or cross-linking. Furthermore, a one-pot copolymerization/“exhaustive” BV post-modification procedure was developed to produce such copolymers in a convenient and scalable manner. This user-friendly methodology is able to access diverse poly(VAc-<i>co</i>-MAM)s including both statistical and narrow-dispersed block copolymers and could greatly facilitate the exploration of applications with such materials.

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