The Journal of Organic Chemistry

Alkynyliodonium salts as alkynylating reagents: direct conversion of alkynylphenyliodonium tosylates to dialkyl alkynylphosphonates with trialkyl phosphites

JS Lodaya, GF Koser

Index: Lodaya, Jayant S.; Koser, Gerald F. Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1513 - 1516

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Citation Number: 44

Abstract

The treatment of various alkynyl (pheny1) iodonium tosylates 1 (R= t-Bu, s-Bu, LPr, cyclopentyl, Ph, and p-MeC6H,; X-= OTs-) with neat trimethyl phosphite gave the dimethyl alkynylphosphonates 4a and 4d-h in isolated yields ranging from 34 to 90%. Similar treatment of 1 (R= t-Bu, X-= OTs-) with neat triethyl and triisopropyl phosphites gave the diethyl and diisopropyl alkynylphosphonates 4b (81%) and 4c (58%). The byproducts of ...