16029-98-4Relevant articles and documents
Evidence for an oxygen anthracene sandwich complex
Klaper, Matthias,Linker, Torsten
, p. 11896 - 11899 (2013)
Oxygen sticks in between acenes: The rate of the photooxygenation of bis(anthryl)alkanes with singlet oxygen shows a maximum for a defined chain length (n=4). In combination with calculations, a bathochromic shift of the UV/Vis absorption for only one endoperoxide and a CT absorption band, this gives considerable evidence for an oxygen anthracene sandwich complex. Copyright
N-aminomethylation vs. C-aminomethylation of indole and pyrrole with an N,O-acetal controlled by the hardness of a counter ion of an iminium compound
Sakai, Norio,Okano, Hidetoshi,Shimamura, Kazuyori,Konakahara, Takeo
, p. 501 - 503 (2014)
Under relatively strong Lewis acidic conditions (a softer counter ion) using TMSOTf and TMSI, the aminomethylation of indole or pyrrole with a typical N,O-acetal preferentially produced the kinetically favored N-aminomethylated indole or pyrrole derivative. Use of a relatively weak Lewis acid (a harder counter ion), such as TMSCl and TMSBr, preferentially produced the thermodynamically favored C-aminomethylated indole and pyrrole derivative.
Evaluation of aroma-active compounds in Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) by gas chromatography-olfactometry, aroma reconstitution, and omission test
Dharmawan, Jorry,Kasapis, Stefan,Sriramula, Praveena,Lear, Martin J.,Curran, Philip
, p. 239 - 244 (2009)
The aroma-active compounds of Pontianak orange peel oil (Citrus nobilis Lour. var. microcarpa Hassk.) were characterized by using gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA) techniques. Forty-one compounds were found to be aroma-active, which were mainly dominated by saturated and unsaturated aldehydes. The flavor dilution (FD) factor was within the range of 2-2048, and compounds having the highest FD factor were α-pinene, β-pinene, linalool, and 2-methoxy-3-(2- methylpropyl) pyrazine, including a few unknown compounds. On the basis of GC-O results, odor activity value (OAV) and relative flavor activity (RFA) were determined for aroma model reconstitution. These resembled the original aroma of the peel oil for the green, fatty, fresh, peely, floral, and tarry attributes, with the model solution derived from OAV being the closest to Pontianak oil. Omission tests were carried out to verify the significance of (Z)-5-dodecenal and 1-phenylethyl mercaptan as key compounds in the aroma of Pontianak orange peel oil.
Unsupported metal silyl ether coordination
Pahl, Jürgen,Elsen, Holger,Friedrich, Alexander,Harder, Sjoerd
, p. 7846 - 7849 (2018)
Simple silyl ethers like O(SiMe3)2 in contrast to normal ethers are inert to metal bonding; however, a “naked”, highly Lewis-acidic, cationic Mg species enforces complexation. DFT calculations indicate that agostic interactions and van der Waals attraction significantly contribute to the stability of this first example of unsupported metal silyl ether coordination.
Synthesis of α-Glucosyl Diacylglycerides as potential adjuvants for Streptococcus pneumoniae vaccines
Hollwedel, Femke,Khan, Ayesha,Maus, Ulrich A.,Stocker, Bridget L.,Timmer, Mattie S. M.
, (2020)
α-Glucosyl diacylglycerols (αGlc-DAGs) play an important role in providing protective immunity against Streptococcus pneumoniae infection through the engagement of the Macrophage inducible C-type lectin (Mincle). Herein, we efficiently synthesised αGlc-DAGs containing C12, C14, C16 and C18 acyl chains in 7 steps and 44–47% overall yields, and demonstrated that Mincle signaling was dependent on lipid length using mMincle and hMincle NFAT-GFP reporter cells. The greatest production of GFP in both cell types was elicited by C14 αGlc-DAG. Accordingly, C14 αGlc-DAG has potential to act as an adjuvant to augment the immune response against S. pneumoniae antigens.
The Ring Opening Reaction of Cyclopolysilanes, (R2Si)n (n=3-6), with Iodine. A Kinetic Study
Watanabe, Hamao,Shimoyama, Hiromi,Muraoka, Tsutomu,Kougo, Yuichi,Kato, Motohiko,Nagai, Yoichiro
, p. 769 - 770 (1987)
Reactions of a series of peralkylcyclopolysilanes with iodine were found to proceed via second-order kinetics.Rate constans show that, in general, the smaller rings react faster than larger rings.Values of the activation parameters, Ea and ΔG, decreased with the decreasing ring size and are parallel with those of the oxidation potentials and of the transition energies.
HALOGEN REDISTRIBUTION REACTIONS BETWEEN ALKYL HALIDES AND TRIMETHYLSILYL IODIDE
Friedrich, Edwin C.,Lucca, George de
, p. 143 - 148 (1982)
Trimethylsilyl iodide has been found to react rapidly at 50 deg C with 1-fluorooctane, 2-fluorooctane and benzyl fluoride to produce the corresponding octyl or benzyl iodides and trimethylsilyl fluoride.Also, it reacts rapidly and cleanly with t-butyl chloride or bromide to form t-butyl iodide.However, it does not react readily with the 1-octyl, 2-octyl, benzyl or allyl chlorides or bromides.We have discovered that tetra-n-butylammonium iodide catalyzes the reactions of primary alkyl chlorides or bromides with trimethylsilyl iodide, and molecular iodine catalyzes the reactions of secondary and tertiary alkyl chlorides and bromides.However, tetra-n-butylammonium iodide slows down the reactions of secondary and tertiary alkyl chlorides and bromides.Mechanistic pathways are suggested for each of the various types of halogen redistribution processes encountered.
Finkelstein Reaction in Non-polar Organic Solvents: A Streamlined Synthesis of Organic Iodides
Takahashi, Yusuke,Seki, Masahiko
, p. 1974 - 1978 (2021)
The Finkelstein reaction of organic halides was found to proceed smoothly in non-polar organic solvents other than acetone when operated in the presence of a catalytic amount of tetra-n-butylammonium bromide and water. The new protocol was successfully applied to a preparation of ethyl 5-iodopentanoate from the corresponding bromide which was used directly for zinc reagent formation and Fukuyama coupling to enable the formation of the (+)-biotin side chain in a streamlined manner. Rate acceleration by microwave irradiation and an application to the synthesis of trimethylsilyl iodide will be described as well.
Efficient method for silylation of p-nitrobenzyl-2-diazoacetoacetate
Tewari, Neera,Rai, Bishwa Prakash,Nizar, Hashim,Singh, Shailendra Kumar
, p. 211 - 214 (2006)
An efficient new method for the silylation of p-nitrobenzyl-2- diazoacetoacetate using hexamethyl disilane and iodine is presented. Copyright Taylor & Francis LLC.
Indium(III) promoted oxidative P-P coupling of silylphosphines
Cartlidge, Ashleigh J.,Matthews, Peter D.
supporting information, (2022/01/28)
The reaction of indium(III) salts with Ph2PSiMe3 and PhP(SiMe3)2 gives rise to a one- and two-electron reductive P-P coupling respectively, with the formation of new P-P bonds resulting in the preparation of (Ph2P)2 and the cyclicoligophosphane compounds (PhP)4 and (PhP)6.
