Preparation of Organomagnesium Compounds

Stereoselective Conjugate Addition Reactions Using In Situ Metallated Terminal Alkynes and the Development of Novel Chiral P,N-Ligands

“…The greater acidity of alkynes can be attributed to the higher s-character of the carbon atom due to its sp-hybridization. 5 Deprotonation of a terminal alkyne can be achieved with strong bases, such as organolithiums, 8 lithium amides, 9 or Grignard reagents 10 (Scheme 1). The metal alkynylides obtained can subsequently be subjected to transmetallation with other metals.…”

Synthesis of All the Stereoisomers of 10,14‐Dimethyloctadec‐1‐ene, 5,9‐Dimethyloctadecane and 5,9‐Dimethylheptadecane, the Sex Pheromone Components of the Apple Leafminer, Lyonetia prunifoliella

“…In field trapping experiments, 1, 2 and 3 singly were unattractive to males, but as ternary mixture attracted numerous male moths. This type of cyclization had been recorded in the cases isomers of 1 can be converted into the stereoisomers of 2 of the Grignard reaction in general [5] and in the case of 5and 3. [1] Each of the hydrocarbons 1, 2 and 3 has two stereogenic centers, and therefore possesses four stereoisomers.…”

Kinetics and mechanism of the C-S coupling reactions of aryl Grignard reagents with aryl arenesulfonates

“…In a jacketed two necked reaction vessel of approximately 25 ml capacity equipped with a reflux condenser and a magnetic stirrer, phenyl tosylate, toluene and internal standard was thermostatted at 90 o C. THF solution of Grignard reagent was added rapidly to initiate the reaction. Aliquots (7)(8)(9)(10)(11) were withdrawn from the homogeneous solution at 15 minute intervals by syringe and were added to a vial containing a quenching solution of aqueous NH 4 Cl solution for hydrolysis and ether.The vial was capped and shaken. Extraction of the remaining phenyl tosylate and products sulfone and phenol to the ethereal phase was found to be essentially quantitative.…”

“…However, the use of organometallic methods are quite limited and they generally depend on the sulfonylation of carbanions with sulfonyl chlorides [8][9][10]. The use of sulfonates as partners in C-S coupling of organometallic reagents are rare (Scheme 1, path a).…”