35281-68-6

Upstream product

• 96-09-3 styrene oxide 
• 628-71-7 1-Heptyne 
• 42017-07-2 1-heptynyllithium 
• 5908-41-8 benzoyltrimethylsilane 
• 111847-83-7 3-(trimethylstannyl)-1,2-octadiene 
• 100-52-7 benzaldehyde 
• 49770-72-1 oct-2-ynyl zinc bromide 
• 141423-58-7 1-Phenyl-1-trimethylsilanyl-non-3-yn-1-ol 
• 141423-59-8 1-Phenyl-1-triisopropylsilanyl-non-3-yn-1-ol 
• 18495-27-7 1-bromooct-2-yne 
• 123290-13-1 phenyltriisopropylsilylmethanone 
• 34498-14-1 1-iodo-2-octyne 
• 20739-58-6 2-octyn-1-ol 

Downstream Products

• 1357170-60-5 (1-azidonon-3-yn-1-yl)benzene 
• 1309456-69-6 2-pentyl-5-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

Theoretical support for the involvement of a radical pathway in the formation of allenylzincs from propargyl iodides and dialkylzincs: Influence of zinc coordination

Propargyl iodides are good precursors for allenylzincs via reaction with diethylzinc, even in nondegassed medium. These reactions proceed via zinc/iodine exchange. Owing to the previously reported detection of propargyl radical by ESR experiments, in this process a radical mechanism was suspected. Calculations of the C-Zn BDEs in allenyl- and propargylzinc species were performed with the CBS-QB3 method to demonstrate that propargyl radicals could undergo homolytic substitution at zinc. The stabilization of allenylzinc derivatives by chelation, made possible by the selection of appropriate ortho-substituted 3-phenylalkynyl iodides as precursors, was shown to influence the regioselectivity of their addition to aldehydes and ketones. The more stabilized the chelated allenylzinc intermediate, the higher the ratio of homopropargylic alcohols.

Regioselective allylation and propargylation using acylsilanes: Facile synthesis of PGE3 and F(3α) methyl ester

Regioselective allylation and propargylation were achieved using acylsilanes as electrophiles and this methodology was applied to the synthesis of PGE3 and F(3α) methyl ester.

Stereo- and regioselective metal salt-catalyzed alkynylation of 1,2-epoxides

A simple, efficient, stereoselective, and highly regioselective method for the synthesis of β-hydroxyacetylenes by the direct opening of 1,2-epoxides with lithium acetylides in anhydrous THF, in the presence of metal salts, is described. This new method a

Selective Propargylation of Carbonyl Compounds with Allenylstannane/Alkyllithium Mixed Reagents

1-Substituted allenyltrialkylstannanes readily undergo transmetalation with an alkyllithium to generate a tetraalkylstannane and an equilibrating mixture of the allenyl- and propargyllithium compounds.The organolithium derivatives react with a variety of aldehydes and ketones at low temperature to give, after aqueous workup, the regioisomeric acetylenic and allenic carbinols in high yields.The degree of the regioselection is highly sensitive to the steric and electronic properties of the carbonyl substrates.Excellent acetylene selectivities are obtainable by combination of the bulky reagents and substrates or by using acylsilanes as carbonyl components.The origin of the regioselectivity is discussed.

Propargyl and Allyl Grignard and Zinc Reagents. Regioselective Alkylation and Its Application to the Synthesis of PGE3 and F3α Methyl Ester

Regioselective propargylation and allylation were achieved using acylsilanes as electrophiles, and this methodology was applied to the synthesis of PGE3 and F3α methyl ester.

AN EFFICIENT METHOD FOR THE ALKYNYLATION OF OXIRANES USING ALKYNYL BORANES

Alkynyl boranes, generated in situ from lithium acetylides and boron trifluoride etherate, were found to react with oxiranes under mild reaction conditions to afford β-hydroxyacetylenes in high yields.