70950-06-0Relevant articles and documents
Synthesis of Elongated Esters from Alkenes
Miura, Tomoya,Funakoshi, Yuuta,Nakahashi, Junki,Moriyama, Daisuke,Murakami, Masahiro
, p. 15455 - 15459 (2018/10/31)
A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible-light irradiation of an ester-stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical species adds onto the carbon–carbon double bond of an alkene to produce an elongated aliphatic ester.
Fluorodecarboxylation, rearrangement and cyclisation: the influence of structure and environment on the reactions of carboxylic acids with xenon difluoride
Ramsden, Christopher A.,Shaw, Maxine M.
experimental part, p. 3321 - 3324 (2009/08/09)
The reactions of structurally diverse carboxylic acids with XeF2 in both CH2Cl2/Pyrex and CH2Cl2/PTFE have been studied. Pyrex appears to be a very effective heterogeneous catalyst for an electrophilic mode of reaction of polarised XeF2, leading to rearrangement, cyclisation and cationic products. In CH2Cl2/PTFE, fluorodecarboxylation is the main mode of reaction, in accordance with previous studies, and may occur via a SET reaction of unpolarised XeF2.
Radical-mediated Carbonylation of Alkyl Iodides in Aqueous Media
Sugiura, Masaharu,Hagio, Hiroyuki,Kobayashi, Shu
, p. 898 - 899 (2007/10/03)
Radical-mediated single carbonylation of alkyl iodides furnishing carboxylic acids proceeded in water using phosphinic acid as a radical initiator in the presence of a surfactant (CTAB). On the other hand, formation of double carbonylation product (α-keto carboxylic acid) along with single carbonylation product was observed for the first time, when the reaction was carried out in aqueous ethanol without any surfactants.
N-ALKOXY-N-ACYLNITRENIUM IONS IN INTRAMOLECULAR AROMATIC ADDITION REACTIONS
Glover, Stephen A.,Goosen, Andre,McCleland, Cedric W.,Schoonraad, Johan L.
, p. 2577 - 2592 (2007/10/02)
N-alkoxy-N-acylnitrenium ions are generated by treatment of N-alkoxy-N-chloroamides with silver ions in ethereal solvents.These intermediates readily cyclise onto aromatic nuclei on alkoxy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ε benzolactams.Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side-chain aromatic rings.The yields and regioselectivities of these reactions have been ascribed to different transition structures for cyclisation onto the acyl and alkoxy side-chains which involve respectively an exocyclic and endocyclic N-O ?-bond.Evidence for this exeptionally high ?-bond character has been obtained from MNDO calculations which predict a ?-bond order of 0.9 and a rotational barrier of 29.7 kcalmol-1
Total Synthesis of a Macrocyclic Pyrrolizidine Alkaloid, (+/-)-Integerrimine, Utilizing an Activable Protecting Group
Narasaka, Koichi,Sakakura, Toshiyasu,Uchimaru, Tadafumi,Guedin-Vuong, Denis
, p. 2954 - 2961 (2007/10/02)
A new esterification reaction has been developed utilizing a (methylthio)methyl (MTM) group as an activable protecting group of carbocyclic acid.A total synthesis of a 12-membered pyrrolizidine alkaloid, (+/-)-integerrimine (1), has been achieved by applying the above method to formation of the macrocyclic bislactone skeleton.The acid anhydride (16b) of the integerrinecic acid derivative was coupled with lithium alkoxide of retronecine silyl ether (5b) in the presence of DMAP to afford the α,β-unsaturated ester.Oxidation of the MTM group afforded an active (methylsulfonyl)methyl ester (28b), which cyclized to give the macrocyclic bislactone 29.
A FACILE SYNTHESIS OF CARBOXYLIC ESTERS AND CARBOXAMIDES BY THE USE OF 1,1'-DIMETHYLSTANNOCENE AS A CONDENSING REAGENT
Mukaiyama, Teruaki,Ichikawa, Junji,Asami, Masatoshi
, p. 683 - 686 (2007/10/02)
Various carboxylic esters or carboxamides are prepared in good yields under nearly neutral conditions from equimolar amounts of free carboxylic acids and alcohols or amines, respectively, by the use of 1,1'-dimethylstannocene as a condensing reagent.
CESIUM FLUORIDE-PROMOTED SYNTHESIS OF CARBOXYLIC ACID DERIVATIVES USING 2-FLUOROPYRIDINIUM SALT
Shoda, Shin-ichiro,Mukaiyama, Teruaki
, p. 391 - 392 (2007/10/02)
In the presence of cesium fluoride, the equimolecular reactions of carboxylic acids with alcohols, amines or thiols using 2-fluoro-pyridinium salt proceeded smoothly under mild conditions to afford the corresponding carboxylic acid derivatives with base s
