1-Acetylene-l-thioethers

Enephosphine sulfides with CuCl s. 26, 715 thioenolethers from 1-acetylene-l-thioethers with CuBr or Cul cf. P. Vermeer, C. de Graaf, and J. Meijer, R. 93, 24 (1974)... 

Ethylmagnesium bromide 1-Acetylene-l-thioethers from sulfenylchlorides... 

Amorphous selenium added in small portions at —33° to a soln. of Na-pro-pynilide prepared from methyl iodide and Na-acetylide in liq. NHg containing suspended NaNH2, then ethyl bromide added immediately 1-ethylseleno-l-propyne. Y 75% based on Se. Also 1-acetylene-l-thioethers and 1-acetylene-1-tellurides s. L. Brandsma, H. Wijers, and J. F. Arens, R. 81, 583 (1962). 

Triazines are generally more reactive in [2 + 4] cycloaddition in comparison with 1,2,3-tria-zines. The wide variety of dienophiles can be employed enamines, enaminones, vinyl silyl ethers, vinyl thioethers, cyclic ketene jV,O-acetals, /V-phenylmaleimide, 6-dimethylaminopentafulvene, 2-alkylidene-imidazolidines (cychc ketene aminals), cyclic vinyl ethers, arynes, benzocyclopropene, acetylenes, and alkenes like ethylene, (Z)-but-2-ene, cyclopentene, cyclooctene and bicyclo[2.2.1]hept-2-ene, hexa-1,5-diene, cycloocta-1,5-diene, diallyl ether, cyclododeca-l,5,9-triene,... 

Besides processes (1) and (2), the reader should be aware that nucleophilic attacks on alkynes are treated in other chapters of this book, dealing with rearrangements, cyclizations, polyacetylenes, cyclic acetylenes and perhaps others. A number of publications overlap with ours in different ways and at different levels -. They treat individual alkynes or families " , e.g. acetylene, diacetylenes , acetylene dicarboxylic esters haloacetylenes , alkynyl ethers and thioethers > ynamines , fluoro-alkynes ethynyl ketpnes , nitroalkynes , etc. synthetic targets, e.g. pyrazoles , if-l,2,3-triazoles , isothiazoles , indolizines S etc. reagents, e.g. nitrones , lithium aluminium hydride , heterocyclic A -oxides - , azomethine ylids - , tertiary phosphorus compounds , miscellaneous dipolar nucleophiles - , etc. The reader will appreciate that all of these constitute alternate entries into our subject. 

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