950758-23-3

Upstream product

• 53724-05-3 1-cyclohexyl-3-(trimethylsilyl)prop-2-yn-1-one 
• 540-63-6 ethane-1,2-dithiol 

Downstream Products

• 920979-34-6 2-cyclohexyl-2-ethynyl-1,3-dithiolane 
• 950758-19-7 2-cyclohexyl-2-hex-1-ynyl-1,3-dithiolane 
• 950758-01-7 7-cyclohexyl-7-(hydroxyisopropyl)-8,11-dithiapentadec-5-yne 
• 950758-00-6 7-cyclohexyl-7-(α-hydroxybenzyl)-8,11-dithiapentadec-5-yne 
• 950757-99-0 7-cyclohexyl-7-(1-hydroxyisopropyl)-8,11-dithiapentadec-5-yne 

Relevant academic research and scientific papers

Iron-promoted elimination of β-thioalkoxy alcohols. Olefination by coupling of a carbonyl group with a dithioacetal

Treatment of propargylic dithiolanes with nBuLi followed by a carbonyl electrophile yields the corresponding propargylic dithioacetals. Upon treatment with 1 equiv of Fe(BCaC)3 and excess MeMgl, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.

A convenient synthesis of propargylic dithioacetals

Treatment of trimethylsilyl-substituted alkynyl ketones with 1,2-ethanedithiol in the presence of BF3·OEt2 in methanol afforded the corresponding dithioacetal. Removal of the silyl group under basic conditions followed by palladium-catalyzed coupling reactions with aryl iodides yielded the corresponding propargylic dithioacetals in excellent yield. Georg Thieme Verlag Stuttgart.