10605-68-2Relevant articles and documents
General synthesis of 2-alkyn-1-ylboronates in excellent isomeric purity
Soundararajan, Raman,Li, Guisheng,Brown, Herbert C.
, p. 8961 - 8964 (1994)
2-Alkyn-1-ylboronates have been synthesized successfully, in excellent isomeric purity, via the in situ homologation of alkyn-1-ylboronates with LiCH2I. The relative reactivities exhibited by various LiCH2X reagents (X = Cl; Br; I) are described.
Gold(I)-catalyzed rearrangement of alkynylaziridine indoles for the synthesis of spiro-tetrahydro-β-carbolines
Yang, Yan-Fang,Li, Lian-Hua,He, Yu-Tao,Luo, Jian-Yi,Liang, Yong-Min
supporting information, p. 702 - 707 (2014/02/14)
Functionalized spiro-tetrahydro-β-carbolines were formed by an efficient gold(I)-catalyzed rearrangement reaction of alkynylaziridine indoles. The reaction involved a Friedel-Crafts type intramolecular reaction of alkynylaziridine indoles, following by hydroamination of aminoallene intermediate.
Coinage metals-catalyzed cascade reactions of aryl alkynylaziridines: Silver(I)-single vs gold(I)-double cyclizations
Kern, Nicolas,Blanc, Aurelien,Miaskiewicz, Solene,Robinette, Michelle,Weibel, Jean-Marc,Pale, Patrick
experimental part, p. 4323 - 4341 (2012/06/18)
Alkynylaziridines carrying an aryl group could be efficiently converted into aminoallenylidene isochromans, isoquinolines, or tetrahydronaphtalenes with silver(I) salts and into 1-azaspiro[4.5]decane derivatives with gold(I) complexes. Mechanistic investi
Silver(I)-Catalyzed deprotection of p -methoxybenzyl ethers: A mild and chemoselective method
Kern, Nicolas,Dombray, Thomas,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick
, p. 9227 - 9235,9 (2012/12/12)
The p-methoxybenzyl protecting group (PMB) on various alcohols and an acid was efficiently and selectively cleaved by the action of a catalytic amount of silver(I) hexafluoroantimonate combined with 0.5 equiv of 1,3,5- trimethoxybenzene in dichloromethane at 40 °C.
Reactivity pattern of bis(propargyloxy) disulfides: Tandem rearrangements and cyclizations
Braverman, Samuel,Pechenick-Azizi, Tatiana,Gottlieb, Hugo E.,Sprecher, Milon
experimental part, p. 1741 - 1750 (2011/07/09)
Thirty-five substituted bis(propargyloxy) disulfides were successfully prepared in good to excellent yields, and their reactivity was found to be strongly dependent on the substitution pattern of the reactant. Inter alia they undergo surprising tandem sigmatropic rearrangements and cycloadditions. Three heretofore unknown product types were isolated and fully characterized: 6,7-dithiabicyclo[3.1.1]heptan-2-one 6-oxide derivatives, two isomeric 1,2-dithiete 1,1-dioxides (α,β-unsaturated four-membered cyclic thiosulfonates) from bis(propargyloxy) disulfides with α- or γ-alkyl-substituted propargyl groups, and two isomeric 2-oxa-5,7-dithiabicyclo[2.2.1]heptane 5-oxides from bis(propargyloxy) disulfides with α-tert-butyl- or α,α-dialkyl-substituted propargyl groups. Georg Thieme Verlag Stuttgart - New York.
Gold(i)-catalyzed rearrangement of aryl alkynylaziridines to spiro[isochroman-4,2′-pyrrolines]
Kern, Nicolas,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick
supporting information; experimental part, p. 6665 - 6667 (2011/06/25)
Alkynylaziridines carrying an aryl group could be efficiently converted to spiro[isochroman-4,2′-pyrrolines] with gold salts as catalysts. This new rearrangement involved a Friedel-Crafts type intramolecular reaction followed by cyclization of the aminoallene intermediate, both initiated by the dual σ and π Lewis acidities of gold.
Intramolecular pyridone/enyne photocycloaddition: Partitioning of the [4 + 4] and [2 + 2] pathways
Kulyk, Svitlana,Dougherty, William G.,Kassel, W. Scott,Zdilla, Michael J.,Sieburth, Scott M.
supporting information; experimental part, p. 2180 - 2183 (2011/06/24)
Chemical equations presented. Intramolecular photocycloaddition (>290 nm) between a 1,3-enyne and a 2-pyridone is far more selective than the intermolecular version; a three-atom linkage both controls regiochemistry and separates the [2 + 2] and [4 + 4] pathways. All four head-to-head, head-to-tail, tail-to-head, and tail-to-tail tetherings have been investigated. Linkage via the ene of the enyne leads to [2 + 2] products regardless of alkene geometry, whereas linkage through the yne results in [4 + 4] cycloadducts. The bridged 1,2,5-cyclooctatriene products of [4 + 4] cycloaddition are unstable and undergo a subsequent [2 + 2] dimerization reaction.
Synthesis and reactivity of divinylselenium dichlorides and dibromides
Braverman, Samuel,Pechenick-Azizi, Tatiana,Gottlieb, Hugo E.,Sprecher, Milon
experimental part, p. 577 - 584 (2011/04/15)
Regio- and stereospecific electrophilic addition reactions of selenium tetrachloride and selenium tetrabromide to propargyl alcohols are reported. (Z,Z)-Bis(β-chlorovinyl)selenium dichlorides were isolated in high yields, and their reactivity was dependen
Selective indium-mediated 1,2,4-pentatrien-3-ylation of carbonyl compounds for the efficient synthesis of vinyl allenols
Park, Jisu,Kim, Sung Hong,Lee, Phil Ho
supporting information; experimental part, p. 5067 - 5070 (2009/05/31)
(Chemical Equation Presented) A highly selective synthetic method of functionalized vinyl allenols was developed from the reactions of various carbonyl compounds with organoindium reagent in situ generated from indium and 1-bromopent-4-en-2-yne derivatives. Treatment of vinyl allenols with gold catalyst, dienophile, or indium trihalide produced the functionalized dihydrofuran, cyclohexene, or 2-halo-1,3-diene derivatives in good to excellent yields.
Preparation of siloxacyclopentene containing 1,3-dienes and their Diels-Alder reactions
Pidaparthi, Ramakrishna R.,Welker, Mark E.
, p. 7853 - 7856 (2008/03/11)
A number of enynyloxy dimethyl and diisopropyl silanes have been prepared and converted into siloxacyclopentene containing 1,3-dienes via intramolecular hydrosilylation of the alkyne functional group. Diels-Alder reactions of these dienes are reported.
