33992-52-8

Upstream product

• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 865351-09-3 1-bromo-3-phenylcyclopropene 
• 76651-92-8 1-phenyl-2-propynyl methanesulfonate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 106-96-7 propargyl bromide 

Downstream Products

• 18942-24-0 4-Phenyl-2,3-butadienenitrile 
• 3780-00-5 1-(3-phenyl-1,2-propadienyl)benzene 
• 69153-22-6 4-ethynylpropylbenzene 
• 75031-47-9 2-phenyl-2,3-hexadiene 
• 109182-95-8 2-phenyl-5,5-dimethyl-2,3-hexadiene 
• 109182-85-6 3-phenyl-4,4-dimethyl-1-pentyne 
• 31508-14-2 penta-1,2,4-trien-1-ylbenzene 
• 181020-78-0 4-phenyl-5-hexyn-1-ol 
• 264597-64-0 3-phenyl-6-hepten-1-yne 
• 2327-99-3 1-phenylpropadiene 
• 69248-81-3 (4,4-dimethylpenta-1,2-dien-1-yl)benzene 
• 64788-21-2 (3-chloropropa-1,2-dien-1-yl)benzene 
• 866412-83-1 1-(methoxycarbonyl)-2-(phenylmethylene)cyclopropanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of new ceramide analogues with allene in the sphingoid backbone

Ceramide is an important sphingolipid which can mediate a diverse range of biological activities. New ceramide analogues with an allene group in the sphingoid backbone were synthesized. The synthesis of the key intermediates involved the LiAlH4

Allylic and allenic halide synthesis via NbCl5- and NbBr 5-mediated alkoxide rearrangements

(Chemical Equation Presented) Addition of NbCl5 or NbBr 5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metallahalo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared by nucleophilic addition, deprotonation, or reduction. Experimentally, the niobium pentahalide halogenations are rapid, afford essentially pure (E)-allylic or -allenic halides after extraction, and are applicable to a range of aliphatic and aromatic alcohols, aldehydes, and ketones. 2009 American Chemical Society.

Generation and stereoselective transformations of 3-phenylcyclopropene

A convenient and inexpensive approach to the generation of 3-phenylcyclopropenes is described. Reaction of these compounds with a range of dienophiles and dipolarophiles led to the stereoselective formation of [4+2]- and [3+2]-cycloadducts, which were exclusively exo-3-phenyl-cis-1,2-disubstituted cyclopropanes. Efficient trapping of 1-lithio-3-phenylcyclopropene with different electrophiles is also discussed. Ab initio calculations suggest that the lowest energy conformation of 3-phenylcyclopropene has the plane of the benzene ring perpendicular to the cyclopropene π-bond but with a low rotation barrier.

Ene reaction of arynes with alkynes

Arynes, generated in situ from ortho-silylaryl triflates, undergo ene reaction with alkynes possessing propargylic hydrogen in the presence of KF/18-crown-6 in THF at room temperature to give substituted phenylallenes. Various terminal and internal alkyne

Generation and stereocontrolled trapping of 3-phenylcyclopropene and its derivatives

Selective methods for the preparation of 3-phenylcyclopropene and its 1-substituted derivatives are provided. The parent cyclopropene is readily trapped in (3+2)- and (4+2)-cycloadditions that lead to exo-3-phenyl-1,2- disubstituted cyclopropanes. Ab initio calculations suggest that the lowest energy conformation has the plane of the benzene ring perpendicular to the cyclopropene π-bond but with a low rotation barrier.