81890-10-0Relevant articles and documents
Electrochemical Reduction of Phenylpropadiene at Mercury Cathodes in Dimethylformamide: Isomerization of the Allene to 1-Phenyl-1-propyne
Chen, Tsu-yu Raymond,Anderson, Mark R.,Grossman, Steven,Peters, Dennis G.
, p. 1231 - 1236 (1987)
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.
Gold(I)-catalyzed rearrangement of propargyl benzyl ethers: A practical method for the generation and in situ transformation of substituted allenes
Bolte, Benoit,Odabachian, Yann,Gagosz, Fabien
scheme or table, p. 7294 - 7296 (2010/08/05)
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.
Highly chemoselective coupling of allenylstannanes with organic iodides promoted by Pd(PPh3)4/LiCl: An efficient method for the synthesis of substituted allenes
Huang, Chih-Wei,Shanmugasundaram, Muthian,Chang, Hao-Ming,Cheng, Chien-Hong
, p. 3635 - 3641 (2007/10/03)
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