13610-06-5Relevant articles and documents
Gold-Catalyzed Oxidative Hydrative Alkenylations of Propargyl Aryl Thioethers with Quinoline N-Oxides Involving a 1,3-Sulfur Migration
Wagh, Sachin Bhausaheb,Singh, Rahulkumar Rajmani,Sahani, Rajkumar Lalji,Liu, Rai-Shung
, p. 2755 - 2758 (2019)
This work reports gold-catalyzed oxidative alkenylations of quinoline N-oxides with propargyl aryl thioethers to afford 3-hydroxy-1-alkylidenephenylthiopropan-2-one via a 1,3-sulfur group migration. The mechanism of this reaction is postulated to involve
Photochemical Doyle-Kirmse Reaction: A Route to Allenes
Or?owska, Katarzyna,Rybicka-Jasińska, Katarzyna,Krajewski, Piotr,Gryko, Dorota
supporting information, p. 1018 - 1021 (2020/01/31)
This Letter describes the metal-free, blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides generated from donor/acceptor diazoalkanes and propargyl sulfides. The reaction furnishes highly functionalized allenes from a broad range of starting materials in decent yield. Mechanistic experiments supported by the literature data suggest singlet carbenes as intermediates in this reaction.
Unique Reactivity of α-Substituted Electron-Deficient Allenes using Sulfinate Salts as Lewis Base Organocatalysts
Martzel, Thomas,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Brière, Jean-Fran?ois,Perrio, Stéphane
supporting information, p. 96 - 106 (2017/01/14)
The efficient sulfinate-catalyzed intermolecular addition reaction of α-substituted allenyl sulfones and allenoates with Michael acceptors is highlighted. The sequence proceeds under mild conditions to provide a scalable and efficient access to versatile
Formal regiocontrolled hydroboration of unbiased internal alkynes via borylation/allylic alkylation of terminal alkynes
Moure, Abraham L.,Mauleon, Pablo,Arrayas, Ramon Gomez,Carretero, Juan Carlos
supporting information, p. 2054 - 2057 (2013/06/04)
In accessing trisubstituted vinyl boronates from terminal alkynes, a propargyl directing (2-pyridyl)sulfonyl group allows terminal alkynes to undergo Cu-catalyzed B2(pin)2-borylation and subsequent Cu-catalyzed allylic alkylation wit
Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine: synthesis of N-allenylsulfenimides.
Armstrong, Alan,Cooke, Richard S,Shanahan, Stephen E
, p. 3142 - 3143 (2007/10/03)
Amination of propargylic sulfides with a ketomalonate-derived oxaziridine under metal free conditions gives N-Boc-N-allenylsulfenimides via [2,3]-sigmatropic rearrangement.
Studies on the Addition of Allyl Oxides to Sulfonylallenes. Preparation of Highly Substituted Allyl Vinyl Ethers for Carbanionic Claisen Rearrangements
Denmark, Scott E.,Harmata, Michael A.,White, Kathleen S.
, p. 4031 - 4042 (2007/10/02)
Thirty-five allyl vinyl ethers bearing an arylsulfonyl anion-stabilizing group have been prepared by addition of allylic alkoxides to (arylsulfonyl)allenes.The allyl vinyl ethers are produced as either β,γ-unsaturated or α,β-unsaturated sulfones depending upon the substitution pattern of the allene and the reaction conditions.A wide variety of substitution patterns are available by using this method.Factors that control the position and stereochemistry of the vinyl ether double bond are discussed.