𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Ketene acetal monomers: Synthesis and characterization

✍ Scribed by J. V. Crivello; R. Malik; Y.-L. Lai

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
822 KB
Volume
34
Category
Article
ISSN
0887-624X

No coin nor oath required. For personal study only.

✦ Synopsis

SYNOPSIS

A new, facile, and high-yield synthesis of ketene acetals derived from readily available and inexpensive starting materials has been developed. For example, an a,@-unsaturated aldehyde can be condensed with an alkane diol to afford a 2-vinyl substituted cyclic acetal. This latter compound can be converted to the desired cyclic ketene acetal by isomerization of the double bond in the presence of tris(triphenylphosphine)ruthenium(II) dichloride. Good to excellent yields of cyclic ketene acetals were obtained employing this method. The novel monomers were fully characterized by IR, NMR, and by elemental analysis. 0 1996 John Wiley & Sons, Inc. Keywords: ketene acetals cyclic ketene acetals isomerization tris(tripheny1-ph0sphine)ruthenium (11) dichloride INTRODUCTION ' Ketene acetals (A) are a well-known class of compounds having the general structure shown below.

Due to the strong electron-releasing effects of the two alkoxy groups, ketene acetals display a pronounced dipolar character that confer on these compounds great reactivity towards electrophiles, nucleophiles, and free radicals.2 Schildknecht3 reported that of ketene acetals are more reactive than the related vinyl ethers in cationic polymerization. McElvain et al.4 observed that ketene acetals undergo facile cationic polymerization even in the presence of such acids as sulfuric acid as an initiator. More recently, the polymerization of ketene acetals under free radical conditions was r e p ~r t e d . ~. ~ It was further shown7 that the polymerizations of cyclic ~~ ~~ ~ ~ ~ ~ ~ ~ ~ ~ ~~

📜 SIMILAR VOLUMES

Cycloaddition Reactions of Ketene Diethy
Cycloaddition Reactions of Ketene Diethyl Acetal toward the Synthesis of Cyclobutene Monomers
✍ Carina S Kniep; Anne B Padias; H.K Hall Jr. 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 152 KB

AbstractÐThe [212]-cycloaddition reactions of ketene diethyl acetal with methyl acrylate and acrylonitrile were optimized. Highly ef®cient ketal cleavage to either 2-cyano-1-cyclobutanone or 2-methoxycarbonyl-1-cyclobutanone was achieved using formic acid. Among the numerous reduction methods attemp

ChemInform Abstract: Cycloaddition React
ChemInform Abstract: Cycloaddition Reactions of Ketene Diethyl Acetal Toward the Synthesis of Cyclobutene Monomers.
✍ Carina S. Kniep; Anne B. Padias; H. K. Hall Jr. 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 35 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Synthesis of ketene S,S-acetals from thi
Synthesis of ketene S,S-acetals from thioamides
✍ T. Harada; Y. Tamaru; Z. Yoshida 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 237 KB

A new method converting thioamides to ketene S,S-acetals, which exhibits wide compatibility with olefin, ketone, ester and amide groups, has been described. Thioamides have proved to be synthetically very potential by the total synthesis of Vitamin Bl2 (construction of corrin molecule) by Woodward a

Synthesis and Characterization of Novel
Synthesis and Characterization of Novel Trifluoromethylphenyl Silane Monomers
✍ Zhanxiong Li; Liping Du; Songqing Tang; Changyao Wang 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 50 KB

Using 3,5-bis(trifluoromethyl)bromobenzene and methyltrimethoxysilane or tetraethoxysilane as raw materials, novel trifluoromethylphenyl silanes were synthesized via Grignard reaction and substitution reaction, and the molecular structure of silane products was characterized by NMR, FT-IR, MS techni

Synthesis and characterization of curabl
Synthesis and characterization of curable methacrylate-based monomers
✍ Mousa Ghaemy; Sara Bekhradnia 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 430 KB 👁 2 views

## Abstract The synthesis of new methacrylate‐based, curable macromonomers, 4,4′‐bis[2‐hydroxy‐3‐aminopropylmethacrylate] diphenyl ether (BHAPE) and 4,4′‐bis[2‐hydroxy‐3‐aminopropylmethacrylate] diphenyl methane (BHAPM), is reported. BHAPE and BHAPM were prepared by the reaction of glycidyl methacr