86983-89-3Relevant academic research and scientific papers
Stability, Kinetic, and Mechanistic Investigation of 1,8-Self-Immolative Cinnamyl Ether Spacers for Controlled Release of Phenols and Generation of Resonance and Inductively Stabilized Methides
Matikonda, Siddharth S.,Fairhall, Jessica M.,Tyndall, Joel D. A.,Hook, Sarah,Gamble, Allan B.
, p. 528 - 531 (2017)
Three cinnamyl ether spacers (non-methyl, α-methyl, and γ-methyl) for caging of phenols have been synthesized and are physiologically stable. When triggered, the γ-methyl spacer releases phenols (pKa 7.8 and 9.8) with a t1/2 a 7.8) with a t1/2 = 27 and 54 min. For the γ-methyl spacer, the results suggest the presence of a resonance and inductively stabilized aza-cinnamyl methide.
Pd-catalyzed regioselective and stereospecific Suzuki-Miyaura coupling of allylic carbonates with arylboronic acids
Li, Chenguang,Xing, Juxiang,Zhao, Jingming,Huynh, Patrick,Zhang, Wanbin,Jiang, Pingkai,Zhang, Yong Jian
supporting information; experimental part, p. 390 - 393 (2012/02/15)
The Pd-catalyzed Suzuki-Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids has been developed in a wet solvent under a base-free system to afford allyl-aryl coupling products in a high level of isolated yields with complete regio- and E/Z-selectivities with good to excellent chemoselectivities. The coupling reaction of optically active allyl carbonates gave allyl-aryl coupling products with excellent enantioselectivities with inversion of the stereochemistry. This coupling method was successfully applied to the synthesis of (S)-naproxen.
Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 3443 - 3452 (2008/02/12)
Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzene-disulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts. Georg Thieme Verlag Stuttgart.
Radical and Ionic Nucleophilic Substitution Reactions on α-Alkyl-γ-(p-nitrophenyl)allyl Derivatives
Barker, Steven D.,Norris, Robert K.
, p. 527 - 544 (2007/10/02)
The nature of the reaction between α-alkyl-γ-(p-nitrophenyl)allyl chlorides (1)-(3), which have the general form p-O2NC6H4CH=CHCH(Cl)R, and a variety of nucleophiles depends on the alkyl group R and the nucleophile.The chloride (1) (R = Me) undergoes ionic (SN2 and subsequent Michael addition) processes with the salt (7) of 2-nitropropane to give products (15) and (16) whereas the chloride (2) (R = Pri) gives a mixture of products (17) and (18) which are shown to arise by a radical-chain nucleophilic substitution process, with allylic rearrangement-an SRN1' reaction- and ionic processes respectively.The chloride (3) (R = But) gives the SRN1' product (25) with the salt (7).Other nucleophiles with (2) and (3) appear to react by ionic (SN2 and SN2') and/or SRN1' processes; e.g. (3) gives an excellent yield of the malononitrile (32) by an SN2' process when treated with the sodium salt (9).
