Howell K. Smith

Iodotrimethylsilane Reduction of Benzoins: Synthesis of Deoxybenzoins and Tetraarylfurans

Abstract Benzoins react readily with iodotrimethylsilane to produce, in many cases, mixtures of deoxybenzoins and tetraarylfurans.

Phase Transfer Free Radical Reactions:1 Polymerization of Acrylic Monomers

The use of phase transfer catalysis (PTC) for the purpose of carrying out ionic reactions has become commonplace in recent years.2 Although the techniques of PTC have been concerned for the most part with the transfer of anionic reagents between two immiscible phases for subsequent nucleophilic reactions, the concept is believed to be much more general.3 Recently, for instance, a few examples describing extension of the process to cationic (electrophilic) reagents have been reported.4,5

A One-Pot Transformation of Ketones Into N-(Meth)Acryloyl-2-Amino Acids

Abstract A synthetic sequence for the preparation of N-(meth)acryloyl-2-amino acids is outlined which involves transformation of a ketone successively into an aminonitrile and a (meth)acrylamidonitrile, followed by selective hydrolysis of the nitrile function. All reactions are performed in aqueous media, in one reaction vessel, and in a stepwise manner without isolation of any intermediate products.

Functional, Telechelic Polymers Derived from Reactions of Nucleophilic Oligomers and Alkeynl Azlactones, Part I: Telechelic Acrylamides Derived from Reactions of Alkeynl Azlactones and Amine-Terminated Oligomers

Because of their cost effectiveness and non-polluting nature, so-called 100% solids resin systems that can be converted to finished product on exposure to either electron beam or ultraviolet radiation are an important and permanent part of our present day technology. Applications for these curable systems are wide and extremely varied, from use as protective coatings on wood, metal, glass, and plastics to adhesives and restoratives used in the repair of teeth2.

Functional, Telechelic Polymers Derived from Reactions of Nucleophilic Oligomers and Alkenyl Azlactones, Part II: Multiazlactones-Alternatives to Isocyanate and Epoxy Resins?

2-Oxazolin-5-ones (azlactones, 1) in general undergo ring-opening addition reactions with a variety of nucleophiles including water, alcohols, amines, and mercaptans.2 Analogous reactions of alkenyl azlactones (1, R1 = vinyl or isopropenyl) with a variety of amines3,4 and alcohols4 have also been reported. In the previous chapter we described the preparation of telechelic acrylamides via reaction of alkenyl azlactones with amine-terminated oligomers. As part of our continuing interest in the utilization of azlactones in polymer chemistry,5 we would like to propose that multiazlactones (Scheme 1) offer considerable potential as alternatives and as complementary reactive resins to the conventional isocyanate and epoxy resin systems in widespread use today. By proper manipulation of starting material substituents and functionalities, the polymer chemist will be able to design linear or crosslinked polymeric materials possessing a range of properties to suit a variety of applications.