81890-10-0

Upstream product

• 917-54-4 methyllithium 
• 657390-90-4 1-phenyl-3-trimethylstannyl-1-propyne 
• 591-50-4 iodobenzene 
• 1004-12-2 N-deutero-N-methyl-aniline 
• 1228107-68-3 (3-benzyloxyprop-1-ynyl)benzene-d2 
• 1228107-73-0 (5-benzyloxypent-3-ynyl)benzene 
• 536-74-3 phenylacetylene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 3355-31-5 1-chloro-3-phenyl-2-propyne 

Downstream Products

• 92885-31-9 C₂₈H₃₇⁽²⁾HS 

Relevant academic research and scientific papers

Electrochemical Reduction of Phenylpropadiene at Mercury Cathodes in Dimethylformamide: Isomerization of the Allene to 1-Phenyl-1-propyne

Polarograms and cyclic voltammograms exhibit two waves for reduction of phenylpropadiene at a mercury electrode in dimethylformamide containing tetra-n-butylammonium perchlorate; the first wave signals reduction of phenylpropadiene to 1-phenyl-1-propene and the second wave is attributable to reduction of 1-phenyl-1-propene to 1-phenylpropane.However, the first wave is abnormally small because phenylpropadiene undergoes substantial rearrangement to 1-phenyl-1-propyne, which is reducible to 1-phenylpropane at nearly the same potential as 1-phenyl-1-propene.Controlled-pot ential electrolyses of phenylpropadiene, 1-phenyl-1-propene, and 1-phenyl-1-propyne at mercury pool cathodes have verified the processes elucidated by means of polarography and cyclic voltammetry.In the presence of diethyl malonate (a proton donor), base-catalyzed isomerization of phenylpropadiene to 1-phenyl-1-propyne is blocked totally; at a potential corresponding to the first wave for reduction of phenylpropadiene, electrolysis products are trans-1-phenyl-1-propene, cis-1-phenyl-1-propene, and 1-phenyl-2-propene, whereas 1-phenylpropane and 1-phenyl-2-propene are obtained at a potential on the second reduction wave for phenylpropadiene.

Propargylic C(sp3)-H Bond Activation for Preparing η3-Propargyl/Allenyl Complexes of Yttrium

Propargylic C(sp3) - H bond activation of 1-substituted-1-propynes, such as 1-trimethylsilyl-1-propyne, 2-hexyne, and 1-phenyl-1-propyne, was achieved by treatment with an alkylyttrium complex 8 bearing an ene-diamido ligand to give the corresponding (η3-propargyl/allenyl)yttrium complexes 7a-c. A unique delocalized η3-propargyl/allenyl structure of these three complexes was revealed by NMR spectroscopy and X-ray single crystal analyses. To elucidate the reactivity of the η3-propargyl/allenyl unit of complexes 7a-c, we conducted two reactions with N-methylaniline and N,N′-dicyclohexylcarbodiimine. For protonation by N-methylaniline, we found that the product distribution of monosubstituted internal alkynes and allenes depended on the substituent on the η3-propargyl/allenyl moiety: 7a and 7b afforded the corresponding internal alkynes as the major products, whereas the major protonation product of 7c was phenylallene. For the insertion of N,N′-dicyclohexylcarbodiimine, complex 7a selectively yielded η3-{N,N′-dicyclohexyl-2-(3-trimethylsilylpropargyl)amidinate}yttrium 12a, while complex 7c produced η3-{N,N′-dicyclohexyl-2-(1-phenylallenyl)amidinate}yttrium complex 13c, though complex 7b gave a mixture of η3-{N,N′-dicyclohexyl-2-(3-normalpropylpropargyl)amidinate}yttrium complex 12b and η3-{N,N′-dicyclohexyl-2-(1-normalpropylallenyl)amidinate}yttrium 13b in an 83:17 ratio. On the basis of the product distributions in these two-types of reactions, (η3-propargyl/allenyl)yttrium complexes were shifted into preferentially favorable η1-allenyl species or η1-propargyl species depending on the substituents prior to the reaction with electrophiles via a four-membered cyclic mechanism.

Gold(I)-catalyzed rearrangement of propargyl benzyl ethers: A practical method for the generation and in situ transformation of substituted allenes

A series of benzyl propargyl ethers react with a gold(I) catalyst to furnish variously substituted allenes via a 1,5-hydride shift/fragmentation sequence. This transformation is rapid and practical. It can be performed under very mild conditions (room temperature or 60 °C) using terminal as well as substituted alkyne substrates bearing a primary, secondary, or tertiary benzyl ether group. The allenes thus formed can be reacted in situ with an internal or external nucleophile, corresponding to an overall reductive substitution process, to produce more functionalized compounds.

Synthesis of heterocyclic allenes via palladium-catalyzed hydride-transfer reaction of propargylic amines

(Chemical Equation Presented) Propargylic diisopropylamines containing heterocycles, which were prepared readily from heterocyclic bromides and propargyldiisopropylamine by the Sonogashira coupling reaction, underwent the allene transformation reaction in

Highly chemoselective coupling of allenylstannanes with organic iodides promoted by Pd(PPh3)4/LiCl: An efficient method for the synthesis of substituted allenes

An efficient method for the preparation of various monosubstituted arylallenes, disubstituted allenes and alkenylallenes via palladium-catalyzed coupling of allenylstannanes with aryl iodides or alkenyl iodides is described. The coupling reaction was carr

Polylithiumorganic compounds -21. On the Deproptonation of 1- and 3-Phenylpropyne as well as Phenylallene with Butyllithium. A Reinvestigation: Three Different Monoanions but one and the same Dianion

In contrast to the literature, with butyllithium only one and the same dianion - namely 7 - is formed starting with each of the three hydrocarbons 1, 4, and 6.On the other hand, upon working at low temperature in tetrahydrofuran as the solvent we were able to detect the three corresponding monoanions 9, 15, and 16, most interestingly 15 and 16 at temperatures higher then -40 deg C show rearrangement with 1,3-hydrogen shift.