4999-58-0

Upstream product

• 22842-10-0 2-methylhept-2-en-6-yne 
• 90252-89-4 p-tolylzinc(II) chloride 
• 16666-80-1 triphenylphosphonio-1-methylethanide 
• 32623-19-1 4-(4'-Methylphenyl)-4-pentenal 
• 5300-06-1 5-methyl-1-(4-methylphenyl)hex-4-en-1-one 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 59553-72-9 5-methyl-1-p-tolylhex-4-en-1-ol 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 6942-61-6 ethyl 4-oxo-4-(p-tolyl)butanoate 
• 66520-90-9 2-(4-methylphenyl)-2-propen-1-ol 
• 66520-91-0 2-(p-Tolyl)-prop-2-enyl vinylether 
• 32623-18-0 4-(4'-Methylphenyl)-4-penten-1-ol 
• 32623-17-9 4-p-tolyl-4-pentenoic acid ethyl ester 
• 2270-59-9 1-bromo-4-methylpent-3-ene 

Relevant academic research and scientific papers

Cyclization-endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst

Triarylpyrylium salts were employed as single electron photooxidants to catalyze a cyclization-endoperoxidation cascade of dienes. The transformation is presumed to proceed via the intermediacy of diene cation radicals. The nature of the diene component was investigated in this context to determine the structural requirements necessary for successful reactivity. Several unique endoperoxide structures were synthesized in yields up to 79%.

Synthesis of Aromatic Bisabolene Natural Products via Palladium-Catalyzed Cross-Couplings of Organozine Reagents

Aromatic bisabolene derivatives were prepared by two methods involving cross-coupling of organozinc reagents. The first synthesis of (±)-glandulone A (10), as well as syntheses of (± )-curcuhydroquinone (8) and (±)-curcuquinone (9), were accomplished via coupling of a secondary alkyl zinc reagent (1,5-dimethyl-4-hexenylzinc halide, 18) to protected bromohydroquinones using Pd(dppf)Cl2 as catalyst. Coupling of arylzinc halides with alkenyl triflate 16 using Pd(PPh 3)4 catalyst provided a number of bisabolene derivatives and led to syntheses of dehydro-α-curcumene (2), (±)-curcuphenol (3), and (±)-elvirol (13). A high-yield synthesis of the (±)-heliannuol D precursor 29 is also reported using this method.

THE REACTION OF BENZYLIC ALCOHOLS WITH CHLOROTRIMETHYLSILANE/DIMETHYL SULPHOXIDE

With catalytic amounts of chlorotrimethylsilane/dimethyl sulphoxide (CTMSO/DMSO) in acetonitrile benzylic alcohols have been found to give high yields of styrenes.By using stoicheiometric amounts of reagents, different reaction pathways are observed: an elimination-addition sequence occurs with secondary and tertiary alcohols affording vicinal dichloro derivatives, β-chloro thioethers and allyl chlorides, whereas a nucleophilic substitution to the corresponding monochlorides occurs starting from primary and sterically hindered substrates.

ORGANIC SYNTHESIS USING HALOBORATION REACTIONS 11. A FORMAL CARBOBORATION REACTION OF 1-ALKYNES AND ITS APPLICATION TO THE DI- AND TRISUBSTITUTED ALKENE SYNTHESIS

The cross-coupling reaction of organozinc chlorides with (Z)-2-bromo-1-alkenylboranes prepared by the bromoboration reaction of 1-alkynes with tribromoborane, proceeds in the presence of a palladium catalyst to give 2,2-disubstituted alkenylboranes, which can be used for the di- or trisubstituted alkene synthesis directly.

Synthetic Studies on Aromatic Sesquiterpenoids: Synthesis of Curcumene Ether by Olefin Cyclisation

The acid-catalysed cyclisation of the olefinic β-hydroxy sulphides (15a) and (15b) gave 3-phenylthiocurcumene ether as a diastereoisomeric mixture together with 5,5-dimethyl-4-phenylthio-1-p-tolylcyclohex-1-ene (16) and 2-methyl-3-(1-methyl-1-phenylthioethyl)-2-p-tolylcyclobutan-1-ol (19).The diastereoisomers (17) and (18) were converted into curcumene ether (24).Treatment of the silyl enol ether (7) with benzenesulphenyl chloride yielded 5-phenylthiomethyl-2-tetrahydrofuran (8) and 5-chloro-1,6-bis(phenylthio)-1-p-tolylhexan-2-one (9). 1-p-Tolylhexane-2,5-dione (10) was also synthesised from (5) employing a palladium-catalysed oxidation, and this result constitutes a formal total synthesis of cuparene (11).