1530-26-3

Upstream product

• 119-61-9 benzophenone 
• 111-66-0 oct-1-ene 
• 100543-37-1 O,O-diethyl octylphosphonothioate 
• 7795-95-1 octane-1-sulfonyl chloride 
• 124-13-0 Octanal 
• 39247-28-4 1,1-dibromonon-1-ene 
• 3958-47-2 triphenylindium 
• 1731-84-6 nonanoic acid methyl ester 
• 112-05-0 nonanoic acid 
• 169138-21-0 6,6-diphenyl-5-hexene-1-ol 
• 927-77-5 n-propylmagnesium bromide 
• 548459-52-5 1,1-diphenyl-6-fluoro-1-hexene 
• 16727-37-0 1,1-Diphenylnonan-1-ol 
• 103687-22-5 ((CH₃)3C₆H₂)2BCHLiC₇H₁₅ 

Downstream Products

• 124-07-2 Octanoic acid 

Relevant academic research and scientific papers

Olefination with Sulfonyl Halides and Esters: Scope, Limitations, and Mechanistic Studies of the Hawkins Reaction

Carbanions of alkanesulfonyl halides and esters react with nonenolizable carbonyl compounds to give olefins. Mechanistic studies reveal that initial aldol-type addition of the carbanions is followed by cyclization-fragmentation to alkenes, and the leaving group on the sulfonyl moiety (RSO2X) controls carbanion stability and rate of the olefin formation.

Ruthenium(II)-catalyzed olefination: Via carbonyl reductive cross-coupling

Natural availability of carbonyl groups offers reductive carbonyl coupling tremendous synthetic potential for efficient olefin synthesis, yet the catalytic carbonyl cross-coupling remains largely elusive. We report herein such a reaction, mediated by hydrazine under ruthenium(ii) catalysis. This method enables facile and selective cross-couplings of two unsymmetrical carbonyl compounds in either an intermolecular or intramolecular fashion. Moreover, this chemistry accommodates a variety of substrates, proceeds under mild reaction conditions with good functional group tolerance, and generates stoichiometric benign byproducts. Importantly, the coexistence of KOtBu and bidentate phosphine dmpe is vital to this transformation.

Palladium-catalysed cross-coupling reactions of triorganoindium reagents with alkenyl halides

The regio- and stereoselectivity of the palladium-catalysed cross-coupling reactions of indium organometallics with stereodefined 1-haloalkenes and 1,1-dihaloalkenes have been studied. Triorganoindium reagents (R3In; R = alkyl, alkenyl, aryl an

Consecutive approach to alkenes that combines radical addition of phosphorus hydrides with horner-wadsworth-emmons-type reactions

(Chemical Equation Presented) Addition of diethyl thiophosphite to terminal alkenes, in the presence of a radical initiator, followed by deprotonation of the phosphonothioate and reaction with a ketone, offers a concise one-pot approach to substituted alkenes. This novel method, which can incorporate alkylation or acylation steps, can be applied to the stereoselective formation of sterically hindered tri- and tetrasubstituted alkenes.

Ni- or Cu-catalyzed cross-coupling reaction of alkyl fluorides with grignard reagents

n-Octyl fluoride underwent a cross-coupling reaction with n-propylmagnesium bromide in the presence of 1,3-butadiene using NiCl2 as a catalyst at room temperature to give undecane in moderate yields. This alkyl-alkyl cross-coupling proceeded more efficiently when CuCl2 was employed instead of NiCl2. Addition of 1,3-butadiene dramatically improved the yields of the coupling products from primary alkyl Grignard reagents in both Ni- and Cu-catalyzed reactions. Alkyl fluorides efficiently reacted with tertiary alkyl and phenyl Grignard reagents using CuCl2 in the absence of 1,3-butadiene to afford the coupling products in high yields. The competitive reaction of a mixture of alkyl halides (R-X; X = F, Cl, Br) with nC5H11MgBr showed that the reactivities of the halides increase in the order R-Cl R-F R-Br. In contrast, in the Cu-catalyzed reaction with PhMgBr, the reactivities increase in the order R-Cl R-Br R-F. Copyright

Hindered organoboron groups in organic chemistry. 23. The interactions of dimesitylboron stabilised carbanions with aromatic ketones and aldehydes to give alkenes

Dimesitylboron stabilised carbanions react with diarylketones to give the corresponding alkenes in mild conditions with good yields. Reactions with aromatic aldehydes are more complex, but in all cases E-alkenes are available in good yields by trapping the intermediates with chlorotrimethylsilane followed by treatment with aq. HF/CH3CN. Treatment of the same intermediates with trifluoroacetic anhydride gives mainly the Z-alkenes. The design and mechanisms of these important processes are considered.

Comparison of Fatty Acid and Polyketide Biosynthesis: Stereochemistry of Cladosporin and Oleic Acid Formation in Cladosporium cladosporioides

Stereochemical aspects of the biosynthesis of the polyketide cladosporin (1) and of oleic acid (2) by Cladosporium cladosporioides NRRL 5507 were compared by use of stable isotope labeling and 2D NMR spectrometry.The absolute stereochemistry of 1 was confirmed by degradation to (2R,6S)-(-)-(6-methyltetrahydropyran-2-yl)acetic acid (12).Incorporations of sodium -, -, -, -, -, and acetates into 1 followed by (13)C NMR analysis of its diacetate 13 provided the biosynthetic pattern of all bonds derived intact from acetate.Deuterium-decoupled (1)H,(13)C shift correlation NMR spectra of 13 derived from acetate showed that deuterium occupies the pro-R position at C-9 and the pro-S position at C-11.Oleic acid (2) obtained from the same incorporation experiment was degraded and derivatized with methyl (S)-(+)-mandelate to afford esters 20 and 21a.Stereospecifically deuterated standard samples 21b and 21c were synthesized.Deuterium-decoupled (1)H,(13)C shift correlation NMR spectra of these compounds demonstrated that during fatty acid biosynthesis in C. cladosporioides the intact carbon-hydrogen bond of acetate is in the pro-R position, the opposite of that at C-11 for the polyketide 1.The possible mechanism of tetrahydropyran ring formation during biosynthesis of cladosporin (1) is discussed.

THE DIMESITYLBORON GROUP IN ORGANIC SYNTHESIS. 4. THE 'BORON WITTIG' REACTION

Anions generated α- to a dimesitylboron group readily condense with aldehydes and ketones.Elimination of Mes2BOLi then leads to alkenes in a boron analogue of the Wittig reaction.