29022-29-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 4116, 1979 DOI: 10.1021/jo01337a021

Upstream product

• 71606-95-6 (1-tert-butyl-pentylidene)-nitro-amine 
• 71607-03-9 (1-tert-butyl-pent-1-enyl)-nitro-amine 
• 2586-89-2 hept-3-yne 
• 3287-02-3 4-(phenylethynyl)toluene 
• 3282-30-2 pivaloyl chloride 
• 763-19-9 2-hydroxy-2-methyl-hept-3-yne 
• 71607-14-2 2,2-dimethyl-heptan-3-one oxime 
• 1942-45-6 4-Octyne 
• 23587-67-9 2,2-dimethyl-4-(triphenylphosphoranylidene)heptan-3-one 
• 29022-24-0 2-methoxy-2-methyl-hept-3-yne 
• 75-16-1 methylmagnesium bromide 

Relevant academic research and scientific papers

Flash Vacuum Pyrolysis of Stabilised Phosphorus Ylides. Part 1. Preparation of Aliphatic and Therminal Alkynes

Thermal extrusion of Ph3PO from β-oxoalkylidenetriphenylphosphoranes 4 to give the alkynes 5, which under conventional pyrolysis conditions is restricted to cases in which R1 is an electron withdrawing group, has been successfully achieved for R1=H or alkyl by using FVP.The method allows convenient construction of multigram quantities of the alkynes 5 from alkyl halides 1 and allows convenient construction of multigram quantities of the alkynes 5 from alkyl halides 1 and acid chlorides 3 in three steps with good overall yields.Under the conditions used the ylides with R2 = cyclobutyl also undergo less of ethene to provide convenient access to the vinylalkynes 6.

A New General Synthesis of Aliphatic and Terminal Alkynes: Flash Vacuum Pyrolysis of β-Oxoalkylidenetriphenylphosphoranes

By using flash vacuum conditions the thermal elimination of Ph3PO from β-oxoalkylidenetriphenylphosphoranes, previously confined to cases with an α-electron withdrawing group, has been extended to provide a general, high yielding synthesis of aliphatic and terminal alkynes.