91890-50-5

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 82737-08-4 N-(phenylselanyl)morpholine 
• 120166-52-1 trans-1-ethoxy-2-(phenylseleno)ethene 
• 2327-99-3 1-phenylpropadiene 
• 1666-13-3 diphenyl diselenide 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 34837-55-3 Phenylselenyl bromide 
• 120166-47-4 cis-1-ethoxy-2-(phenylseleno)ethene 
• 100-52-7 benzaldehyde 
• 5707-04-0 Phenylselenyl chloride 
• 213456-78-1 C₁₉H₂₂O₂Se 
• 104-55-2 3-phenyl-propenal 
• 210416-78-7 (Z)-3-Ethoxy-1-phenyl-2-phenylselanyl-prop-2-en-1-ol 

Downstream Products

• 210416-96-9 (1Z,4Z)-1-Ethoxy-5-phenyl-2,4-bis-phenylselanyl-penta-1,4-dien-3-ol 
• 91890-58-3 ethyl (2E,4Z)-5-phenyl-4-phenylselanylpenta-2,4-dienoate 
• 1071115-55-3 1,3-diphenyl-2-phenylselanylprop-2-en-1-ol 
• 1071115-82-6 4-methyl-1-phenyl-2-phenylselanylhex-1-en-3-ol 
• 1071115-87-1 4,4-dimethyl-1-phenyl-2-phenylselanylpent-1-en-3-ol 
• 218965-46-9 4-phenyl-3-phenylselanylbut-3-en-2-ol 
• 1071115-60-0 1-(4-methoxyphenyl)-4-phenyl-2-phenylselanylprop-2-en-1-ol 
• 1071115-77-9 1-phenyl-2-phenylselanylhept-1-en-3-ol 
• 91890-59-4 C₂₂H₁₈Se 
• 105378-44-7 1,4-diphenyl-2-phenylselanylbuta-1,3-diene 
• 105378-43-6 C₁₆H₁₃ClSe 
• 91890-57-2 C₁₆H₁₃ClSe 
• 91890-55-0 (2E,4E)-5-Phenyl-4-phenylselanyl-penta-2,4-dienoic acid ethyl ester 

Relevant academic research and scientific papers

Meyer-Schuster-Type Rearrangement of Propargylic Alcohols into α-Selenoenals and -enones with Diselenides

We describe a mild and broadly applicable protocol for the preparation of a diverse array of multisubstituted α-selenoenals and -enones from readily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, which enables selenenylation/rearrangement of a variety of propargylic alcohols. Gram-scale experiments showed the potential of this synergistic protocol for practical application.

Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant

The synthesis of regio- and stereoselective aryl substituted α,β-unsaturated aldehydes and ketones from activated allenes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air and triggered by visible light. The same starting materials under ideal anaerobic conditions led to the 2,3-diphenylselenation adduct with no trace of oxygenated products, demonstrating dissolved oxygen as a chemical switch for two different reaction pathways. The salient feature of this protocol is the single electron transfer (SET) achieved by irradiation of one of two organic molecules thereby avoiding a sensitizer to form a radical ion pair.

Selenylated dienes: synthesis, stereochemical studies by 77Se NMR, and transformation into functionalized allenes

2-Phenylselanyl-1,3-dienes 3-8 were prepared by a Wittig or Wittig-Horner-Emmons procedure starting from α-phenylselanyl α,β-unsaturated aldehydes. Ratio and configuration of each diene isomers were determined by 77Se and 1H NMR. The

Phenyltelluroacrylonitriles and phenylselenoacrylonitriles as precursors of (Z)-α-phenylseleno-α,β-unsaturated aldehydes, β-amino-α-phenylselenonitriles and Diels-Alder adducts

Reaction of cyanomethylphosphonate with aryl selenenyl (or tellurenyl) halides and aldehydes, under basic conditions, provides α-phenylseleno or α-phenyltelluro acrylonitriles in good yields. Reaction of the α-phenylseleno acrylonitriles with dienes furnishes the corresponding adducts while reaction with amines furnishes α-phenylseleno-β-amino nitriles. Selective reduction of the cyano group with DIBAL-H results in the α-phenylseleno-α,β-unsaturated aldehydes.

The First Example of the 1-Chalcogene-Substituted Formylolefination of the Ketones and Aldehydes Using 1-Lithio-2-ethoxyvinyl Chalcogenides

The α-chalcogene-substituted formylolefinations of ketones and aldehydes proceeded using 1-lithio-2-ethoxyvinyl chalcogenides/PPSE or TMSOTf to produce the α-chalcogenoformylolefinated products 4a-l in high yields. Tandem-formylolefmation provided the (2Z,4Z)-2,4-bis(chalcogeno)pent-2,4-dienals 5d,h,i and (2Z,4Z,6Z)-2,4,6-tris(phenylthio)hept-2,4,6-trienal derivatives 7d and 8d, respectively.

A New 1-Alkoxy-2-(chalcogeno)allylic or 1-Alkoxy-2,4-bis(chalcogeno)penta-2,4-dienyl Cation: Highly-Regioselective Allylating or Penta-2,4-dienylating Electrophiles and Their Reactions

2-(Chalcogeno)-1-ethoxyallylic cations 4A are easily generated from the reactions of 2-(chalcogeno)- 1-ethoxyprop-l-en-3-ols 2a-e or 2-(chalcogeno)prop-2-enal acetals 3a-c and TMSOTf and reacted with various nucleophiles to give the adducts 5a-8a, 5b-11b, and 5c-e regio and stereoselectively. 2,4-Bis(chalcogeno)penta-2,4-dienal acetals 16a,c and the 2,4,6-tris(phenylthio)hepta-2,4,6-trienal acetal 20c also gave the dienones 17a,c and 21c in good yields. Furthermore, the intramolecular cyclization of the alkenyl alcohols 25a,b and the 2,4-dienal 2,4-dinitrophenyl hydrazones 29a - c afforded the tetrahydrofurans 26a,b and 3,5-bis(chalcogeno)pyridines 30a-c, respectively.

Preparations de composes α-arylselenocarbonyles a l'aide de morpholinoareneselenenamides

The reactivity of the morpholinoareneselenenamides 1 which are readily prepared from various diaryldiselenides, is investigated.The selenenamides 1 are good α-selenenylating agents for aliphatic aldehydes, α-ketoesters and conjugated enals yielding the α-

SYNTHESE D'α-HYDROXYALLENES α-FONCTIONNALISES A PARTIR D'α-PHENYLSELENOENALS

Morpholinobenzeneselenenamide (MBSe) react with enals to form α-phenylselenoenals which undergo Wittig and Horner reactions.We synthetise 1-substituted 3-phenylseleno-1,3-butadienes.Oxidation and subsequent 2,3-sigmatropic rearrangement lead to α-fonctionnalized α-hydroxyallenes.This compounds give access to 2,5 dihydrofurans.