29372-98-3Relevant academic research and scientific papers
Bulky, spherical, and fluorinated anion BArF induces 'on-water' activity of silver salt for the hydration of terminal alkynes
Saha, Sayantani,Sarbajna, Abir,Bera, Jitendra K.
supporting information, p. 1444 - 1447 (2014/03/21)
AgBArF displays remarkable 'on-water' activity for catalytic hydration of terminal alkynes although it is ineffective in common organic solvents. Liquid alkynes do not require additive or co-solvent whereas a small amount of ethyl acetate triggers quantitative conversions for solid alkynes.
AgOTf catalyzed hydration of terminal alkynes
Das, Rima,Chakraborty, Debashis
, p. 722 - 726 (2013/02/22)
The silver catalysis towards the hydration of terminal alkynes is explored using Silver(I) triflate (AgOTf). The reaction leads to the formation of only Markovnikov addition product with excellent yield. Copyright
Unusual reaction leading to the formation of dienylamides
Gridnev, I. D.,Balenkova, E. S.
, p. 40 - 42 (2007/10/02)
The reaction of the acetyl fluoroborate-acetonitrile complex with cyclohexene leads at the first stage to the protonated β,γ-unsaturated ketone, which is capable of reacting with acetonitrile to form 3-(1-acetylaminoethylidene)cyclohexene.By changing the order of addition of the reagents it is possible to obtain good yields of dienylamides based on cyclohexane and 1-hexene.
A HIGHLY SELECTIVE ONE-CARBON RING ENLARGEMENT REACTION DIRECTED BY SILICON
Tanino, Keiji,Katoh, Tetsuya,Kuwajima, Isao
, p. 1815 - 1818 (2007/10/02)
On treatment with dichloroaluminium phenoxide, 1-(trimethylsilyl)methylcycloalkanecarbaldehydes undergo selective rearrangement of ring carbons to give the corresponding one-carbon ring enlarged 2-(trimethylsilyl)methylcycloalkanones in excellent yields.
Synthesis with Organoboranes; 4. Transformation of Olefins into Homoallylic Alcohols, β,γ- and α,β-Unsaturated Ketones via Allylic Diethylboranes
Zaidlewicz, Marek
, p. 701 - 703 (2007/10/02)
Allylic diethylboranes are obtained from 1-methylcycloalkenes and 2-alkenes, respectively, via metalation with trimethylsilylmethylpotassium (generated in situ from bis(trimethylsilylmethyl)mercury and potassium sand) and subsequent reaction with chlorodiethylborane.The allylic boranes react diastereoselectively with aldehydes to give homoallylic alcohols.The alcohols are oxidized with pyridinium dichromate to β,γ-unsaturated ketones, which in turn are isomerized with aluminum oxide to conjugated ketones.The transformation provides access to 2-methylene-1-acylcycloalkanes, 3-acyl-1-alkenes and 3-acyl-2-alkenes not readily available by Friedel-Crafts acylation of olefins.
ACETYL FLUOROSULFONATE - GENERATION FROM ACETYL FLUORIDE AND SULFUR TRIOXIDE AND REACTIONS WITH OLEFINS
Shastin, A. V.,Balenkova, E. S.,Sorokin, V. D.,Koz'min, A. S.,Zefirov, N. S.
, p. 1039 - 1045 (2007/10/02)
The acylation of methylenecyclobutane, styrene, and vinylcyclopropane by acetyl fluorosulfonate, generated in situ from acetyl fluoride and sulfur trioxide, followed by treatment with methyl or propyl alcohols leads to the products from conjugate addition (alkoxy ketones) in addition to elimination products (α,β-unsaturated ketones).The employed methods makes it possible to separate the stages of addition of the acetyl group and the external nucleophile through the intermediate formation of covalently bonded alkyl fluorosulfonates.
Regiospecific Synthesis of β, γ-Unsaturated Ketones from Allylic Alcohols. Claisen Rearrangement of α-Allyloxy Ketone Enol Derivatives
Kachinsky, Joseph L. C.,Salomon, Robert G.
, p. 1393 - 1401 (2007/10/02)
β,γ-Unsaturated ketones are prepared with regiospecific C-C bond formation at the former γ-position of primary, secondary, or tertiary allylic alcohol precursors by a process involving sigmatropic Claisen rearrangement of intermediate α-allyloxy ket
(Phosphine)carbonylnitrosylacylcobaltate Complexes as Acyl Transfer Reagents. Acylation of Allylic Halides, Conjugated Enones, and Quinones
Hegedus, Louis S.,Perry, Robert J.
, p. 4955 - 4960 (2007/10/02)
The complex Co(NO)(CO)2(PPh3) is an air stable, easily handled crystalline solid, prepared from Co2(CO)8, sodium nitrite, and triphenylphosphine without isolation of the volatile intermediate Co(NO)(CO)3.Treatment of this complex with organolithium reagents at -40 deg C generated unstable acylate complexes - which readily transferred the acyl group to allylic halides to produce β,γ-unsaturated ketones, to conjugated ketones to produce 1,4-dicarbonyl compounds, and to quinones to form 4-acylcyclohexadienones.
Acetylation de trimethylsilyl bicyclo(n,1,0)alcanes : nouvelles syntheses de l'acetyl cyclohexene-2 et d'acetyl bicyclo(n,1,0)alcanes
Ahra, M.,Grignon-Dubois, M.
, p. 820 - 824 (2007/10/02)
Acetylation of trimethylsilyl bicyclo(n,1,0)alkanes was studied using the CH3COCl/AlCl3 complex.The results showed that both larger cycle size (n = 3, 4 or 6) and stereochemistry of the substrate (SiMe3 group in endo or exo position) played a prominent role in the orientation of the reaction : depending upon the starting products, either bicyclic or ethylenic and/or chloro ketones were formed.The results can be rationalized in terms of steric hindrance considerations.They allowed us to propose a new convenient synthesis of acetyl bicyclo(n,1,0)alkanes and also of 1-acetyl 2-cyclohexene.
ACYLATION OF ALKENES WITH ACETYL FLUOROBORATE IN THE PRESENCE OF ACETIC ACID ANHYDRIDE
Shastin, A. V.,Balenkova, E. S.
, p. 870 - 872 (2007/10/02)
The acylation of styrene, vinylcyclopropane, methylenecyclobutane, and isobutylene with acetyl fluoroborate in the presence of acetic anhydride takes place as the conjugate addition of the acetyl and acetoxy groups and leads to preparative yields of the corresponding acetoxy ketones.
