John Cunningham O'toole

Recent Advances in the Synthesis and Applications of Benzo[b]thiophenes

Abstract Recent developments in the application and synthesis of benzo[b]thiophenes are reviewed, with an emphasis on various cyclization methodologies leading to the heterocyclic core structure.

An efficient and practical synthesis of diphenyl cyanomethylenephosphonate: Applications to the stereoselective synthesis of cis-α,β-unsaturated nitriles

Abstract Diphenyl cyanomethylenephosphonate (PhO) 2 POCH 2 CN was prepared as a stable crystalline solid in high yield in a single step from acetonitrile, LDA, and (PhO) 2 P(O)Cl. The potassium ylide generated from this compound afforded α,β-unsaturated nitriles upon reacting with aldehydes, with a stereoselectivity of 64–100% favoring the cis -isomer.

Triethylamine poly(hydrogen fluorides) in the synthesis of a fluorinated nucleoside glycon

The stereospecific synthesis of 6 via a highly selective, noncorrosive fluorination of 4 with Et3N·3HF was discovered. The intermediate fluorosulfonate 5 was isolated, purified and its structure verified.