Moore reaction

For reviews on the transformation of dibromocyclopropanes to allenes (see so-called Doering-Skattebol-Moore reaction) see (a) Hopf H (1980) In Patai S (ed) The Chemistry of Ketenes, Allenes and Related Compoimds Wiley, New York, Part 2, Chapter 2, p 779 ... 

This reaction was first reported by Moore in 1985. It is a synthesis of phenol (or quinone) derivatives by means of the thermal cyclization of enyne-ketenes between C2 and Cy via an aryl/phenoxy biradical intermediate. Therefore, it is generally known as the Moore cyclization. Occasionally, it is directly referred to as the Moore reaction. 

The synthetic utility of the Moore reaction can be illustrated by the efficient synthesis of coenzyme Qo (84%, not illustrated) or aurantioglio-cladin 19 (described above, Chapter 4.12.4). ... 

The Moore reaction is also effective for the synthesis of annulated derivatives of quinines. Moore et al. have established that 4-alkynyl cyclobutenones are precursors in the efficient syntheses of some members of the family of naturally occurring isochroman-1,4-naphthoquinones, which show biological activity as antibiotics and antymycotics. Benzocyclo-... 

L. Bateman and C. G. Moore, Reactions of sulfur with olefins,... 

Green W H, Moore C B and Polik W F 1992 Transition states and rate constants for unimolecular reactions Ann. Rev. Phys. Chem. 43 591-626... 

Polik W F, Guyer D R, Miller W H and Moore C B 1990 Eigenstate-resolved unimolecular reaction dynamics ergodic character of Sq formaldehyde at the dissociation threshold J. Chem. Phys. 92 3471-84... 

Moore C B and Smith I W M 1996 State-resolved studies of reactions in the gas-phase J. Phys. Chem. 100 12 848... 

Moore, J. W. Pearson, R. G. Kinetics and Mechanism, 3rd Ed. John Wiley Sons New York, 1981. Schmid, R. Sapunov, V. N. Non-Formal Kinetics In Search for Chemical Reaction Pathways Verlag Chemie Weinheim, 1982. 

The temperature dependence of a rate is often described by the temperature dependence of the rate constant, k. This dependence is often represented by the Arrhenius equation, /c = Aexp(- a/i T). For some reactions, the temperature relationship is instead written fc = AT" exp(- a/RT). The A term is the frequency factor for the reaction, which reflects the number of effective collisions producing a reaction. a is known as the activation energy for the reaction, and is a measure of the amount of energy input required to start a reaction (see also Benson, 1960 Moore and Pearson, 1981). 

Miller RJ, Smith CR, DeMaster DJ, Pomes WL (2000) Feeding selectivity and rapid particle processing by deep-sea megafaunal deposit feeders A " Th tracer approach. J Mar Res 58 653-573 Moore RM, Hunter KA (1985) Thorium adsorption in the ocean - reversibility and distribution amongst particle sizes. Geochim Cosmochim Acta 49 2253-2257 Moore RM, Millward GE (1988) The kinetics of reversible Th reactions with marine particles. Geochim Cosmochim Acta 52 113-118... 

Diisopropyl methylphosphonate is an organophosphate compound that was first produced in the United States as a by-product of the manufacture of the nerve gas isopropyl methylphosphonofluoridate (GB, or Sarin) (ATSDR 1996 EPA 1989 Robson 1977, 1981). It is not a nerve gas and is not a metabolite or degradation product (Roberts et al. 1995). Diisopropyl methylphosphonate constitutes approximately 2-3% of the crude GB product, but it is neither a metabolite nor a degradation product of GB (EPA 1989 Rosenblatt et al. 1975b). Diisopropyl methylphosphonate is not normally produced except for its use in research. One method of producing diisopropyl methylphosphonate is to combine triisopropyl phosphite and methyl iodide. The mixture is then boiled, refluxed, and distilled, yielding diisopropyl methylphosphonate and isopropyl iodide (Ford-Moore and Perry 1951). Diisopropyl methylphosphonate may also be prepared from sodium isopropyl methylphosphonate by a reaction at 270° C, but a portion of the resulting diisopropyl methylphosphonate is converted to trimethylphosphine oxide at this temperature (EPA 1989). 

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