2397-59-3

Upstream product

• 67-56-1 methanol 
• 63688-80-2 2,3-epoxy-2,3-diethyl-2,3-dihydro-[1,4]naphthoquinone 
• 105-37-3 Ethyl propionate 
• 130-15-4 [1,4]naphthoquinone 
• 109-60-4 1-Propyl acetate 
• 928-49-4 hex-3-yne 

Relevant academic research and scientific papers

The preparation and evaluation of electron poor benzylidene Fischer carbene complexes: Studies toward the total synthesis of (+)-olivin

The continued exploration into the fate of the benzannulation reaction is put forth using the electronic nature of substituents on the aryl ring of benzylidene Fischer carbene complexes as a handle to predict, using σ-para values as a guide, the outcome of the reaction based on the accepted mechanism. The design of this work focuses on evaluation of the synthetic utility of the benzannulation reaction and the means by which this reaction may be improved to be a better synthetic tool in the preparation of complex natural products as this is illustrated in our ongoing total synthesis of (+)-olivin which uses the benzannulation reaction as the key convergent synthetic step. To accomplish these tasks, the preparation of several electron poor benzylidene Fischer carbene complexes was carried out and their reaction with simple alkyne substrates studied. While much is known about the preparation of electron rich benzylidene Fischer carbene complexes, little is known about the preparation of their electron poor counterparts. Thus efforts toward developing useful preparative methods of these elusive targets has also been studied. While the use of both carbon and oxygen based aryl substituents has been explored, to date the preparation of benzylidene carbene complexes containing oxygen based aryl substituents has been exploited to a greater degree since these systems carry more immediate synthetic importance. This is so because the skeletal core of many of the natural products that have been targeted with the benzannulation reaction including (+)-olivin contain a highly oxygenated polycyclic aromatic core. The enhancement in efficiency of the benzannulation reaction using this synthetic methodology is demonstrated by the successful completion of the convergent synthetic step in the total synthesis of (+)-olivin. (C) 2000 Published by Elsevier Science Ltd.

The effects of phosphine ligands on the benzannulation reaction of molybdenum carbene complexes with alkynes

The effects of phosphine substitution at the metal on the reactions of group 6 pentacarbonyl Fischer carbene complexes with alkynes have been found not to be those expected from what is known about these reactions. The product distribution for the reaction of the molybdenum complex 5 with 3-hexyne changes dramatically from predominately indene product to predominately quinone product upon substitution of one of the CO ligands in 5a with a tri-n-butylphosphine.

ELECTRON-TRANSFER PROCESSES: MECHANISMS OF OXIDATION OF ETHERS AND ESTERS BY SILVER-CATALYZED PEROXYDISULPHATE

Nucleophilic carbon-centred radicals, generated from the oxidation of diethyl ether, ethyl acetate, propyl acetate, ethyl propionate, diethyl oxalate and 2-phenylethyl acetate by silver-catalyzed decomposition of peroxydisulphate, have been trapped, mostly by naphthoquinone and in a few cases by protonated quinoline. Characterization of the intermediate radicals allows the rationalization of the mechanism of these oxidations, which are likely to occur through an initial electron-transfer step by Ag(II).

Substrate regulation of product distribution in the reactions of aryl chromium carbene complexes with alkynes

The reactions of arylcarbene complexes with alkynes were examined for six of the nine possible substitution patterns for mono- and dioxygenated aryl substituents of the carbene carbon. The product distributions were found to be highly dependent on a numbe

Solvent, chelation and concentration effects on the benzannulation reaction of chromium carbene complexes and acetylenes

The reactions of a number of chromium carbene complexes (CO)5Cr=C(OMe)R (R = Ph, o-OMePh, p-OMePh, o-O-tBuPh, 1-C6H9, 1-C5H7O) were examined with a variety of acetylenes (R'CCR2, R1, R2 = H, Me, Et, n-Pr, Ph, SiMe3) in sol

PHOTOCHEMICAL REACTION OF EPOXYNAPHTHOQUINONES WITH ALCOHOLS. AN IONIC TRAPPING OF CARBONYL YLIDES

Irradiation of several 2,3-dialkyl-2,3-epoxy-2,3-dihydro-1,4-naphthoquinones in the presence of alcohol gave ring-contracted alcohol-adducts via nucleophilic addition of alcohol to carbonyl ylides.