130233-13-5Relevant articles and documents
Efficient synthesis of 8,11-dimethylene-bicyclo[5.3.1]undecan-2-one
Gu, Haining,Xu, Wei Ming,Kinstle, Thomas H.
, p. 6449 - 6451 (2005)
We report here, an effective methodology for the preparation of 8,11-dimethylene-bicyclo[5.3.1]undecan-2-one. The key steps in these reactions were chloromethylation, cationic-alkyne cyclization and anionic fragmentation sequence.
Single Electron Transfer Mechanism in the Reaction of 1,3-Dithianyllithium and Alkyl Iodides
Juaristi, Eusebio,Jimenez-Vazquez, Hugo A.
, p. 1623 - 1630 (1991)
The reaction between 2-lithio-1,3-dithiane and optically active (R)-2-iodooctane was found to proceed with complete inversion of configuration.This result suggests that the SN2 (rather than single electron transfer (SET)) mechanism is the preferred pathway for reaction between dithianyllithium and unhindered alkyl halides.When the neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene was used as the substrate halide, 6-11percent cyclized alkylated product was obtained.This result suggests that when the SN2 pathway is blocked, SET mechanisms become operative to some extent, at least with iodide as the halogen.The reaction of dithianyllithium and (R)-2-iodooctane and 5,5-dimethyl-6-iodo-1-hexene, with hexane as the solvent, proceeds under heterogeneous conditions to bring about complete racemization of the respective iodide.These results demonstrate for the first time that 2-lithio-1,3-dithiane can act as electron donor in reactions initiated by electron transfer to alkyl iodides.
Stereoselective total syntheses of 9(S)- and 9(R)-HETE
Yadav,Bhanu,Dutta, Dinah
, p. 3929 - 3934 (1998)
A simple and efficient stereoselective total synthesis of methyl 9(S)- and 9(R)-hydroxy -5(Z), 7(E), 11(Z), 14(Z)-eicosatetraenoates using base induced opening of chiral 2.3-epoxy chlorides is described.
Self-assembly and solid-state polymerization of butadiyne derivatives with amide and trialkoxyphenyl groups
Kikuchi, Kohei,Tatewaki, Yoko,Okada, Shuji
supporting information, p. 298 - 305 (2017/05/10)
Three butadiyne derivatives with amide and tri(dodecyloxy)-phenyl (TDP) groups were synthesized, and four solidification methods were applied to obtain their self-assembling states in various conditions. The solids obtained were characterized by the solid-state polymerization behaviors, stretching vibration wavenumbers of N-H bonds of amide groups, powder X-ray diffraction, the thermal behaviors, and scanning electron microscope (SEM) observations. We found that all compounds had at least two polymorphs. Property differences between two polymorphs depended on the compounds. Two compounds showed clear differences in UV-vis spectra of the photo-polymerized solids, i.e., the polydiacetylene (PDA) structure, and irregularly polymerized form, or two PDA structures. The remaining compound showed the same PDA absorption but the monomer melting points were different. All compounds gave the gels in various organic solvents because of the molecular design with amide and TDP groups. SEM observation clarified the relationship between gel appearance and the nanostructures.
Arylation of [6,6]-spiroacetal enol ethers: Reactivity and rearrangement
Aumann, Kylee M.,Healy, Peter C.,Coster, Mark J.
supporting information; experimental part, p. 1070 - 1073 (2011/03/22)
Attempts to selectively arylate [6,6]-spiroacetal enol ethers at the 2-position delivered unexpected results. Palladium-mediated arylation conditions afforded the double-Heck product, whereas reaction with benzenesulfinic acid resulted in a facile rearrangement into the corresponding 5-phenylsulfonyl-3,4, 5,6-tetrahydrochromans, providing access to 5-aryl-3,4,5,6-tetrahydrochroman and hexahydrochroman derivatives.
