EurekaMag
+ Most Popular
Cunninghamia lanceolata plantations in China
Mammalian lairs in paleo ecological studies and palynology
Studies on technological possibilities in utilization of anhydrous milk fat for production of recombined butter-like products
Should right-sided fibroelastomas be operated upon?
Large esophageal lipoma
Apoptosis in the mammalian thymus during normal histogenesis and under various in vitro and in vivo experimental conditions
Poissons characoides nouveaux ou non signales de l'Ilha do Bananal, Bresil
Desensitizing efficacy of Colgate Sensitive Maximum Strength and Fresh Mint Sensodyne dentifrices
Administration of fluid by subcutaneous infusion: revival of a forgotten method
Tundra mosquito control - an impossible dream?
Schizophrenia for primary care providers: how to contribute to the care of a vulnerable patient population
Geochemical pattern analysis; method of describing the Southeastern limestone regional aquifer system
Incidence of low birth weights in a hospital of Mexico City
Tabanidae
Graded management intensity of grassland systems for enhancing floristic diversity
Microbiology and biochemistry of cheese and fermented milk
The ember tetra: a new pygmy characid tetra from the Rio das Mortes, Brazil, Hyphessobrycon amandae sp. n. (Pisces, Characoidei)
Risk factors of contrast-induced nephropathy in patients after coronary artery intervention
Renovation of onsite domestic wastewater in a poorly drained soil
Observations of the propagation velocity and formation mechanism of burst fractures caused by gunshot
Systolic blood pressure in a population of infants in the first year of life: the Brompton study
Haematological studies in rats fed with metanil yellow
Studies on pasteurellosis. I. A new species of Pasteurella encountered in chronic fowl cholera
Dormancy breaking and germination of Acacia salicina Lindl. seeds
therapy of lupus nephritis. a two-year prospective study

The chemistry of compounds derived by microbial oxidation of benzene and derivatives cycloadditions involving 1 2 isopropylidenedioxycyclohexadienes


The chemistry of compounds derived by microbial oxidation of benzene and derivatives cycloadditions involving 1 2 isopropylidenedioxycyclohexadienes



Journal of the Chemical Society Perkin Transactions I 5: 1255-1264



DOI: 10.1039/p19910001255

Various cycloadditions involving the cyclohexadiene derivatives 7-10 have been investigated. Diels-Alder reactions involving dimethyl acetylenedicarboxylate, nitrosobenzene and N-ethylmaleimide gave the adducts 11-14, 16-17 and 18-23 respectively. Hydrolysis of the tricyclic compound 11 with pig liver esterase provided the optically active monoester 15. Tropone, and three carbenes reacted with the diene 7 to give the polycyclic compounds 24 and 29, 31 and 33 as expected. The structure of the adduct 24 was elucidated by X-ray crystallography. The ester 32 was converted into the lactone by way of an oxa-Cope rearrangement of the aldehyde 34. The dienes 7 and 8 reacted with diphenylketene in an unexpected fashion giving the enol ethers 27 and 28 as well as the expected [2 + 2] cycloaddition products 25 and 26.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 007877290

Download citation: RISBibTeXText

Related references

The chemistry of compounds derived by microbial oxydation of benzene and derivatives : cycloadditions involving 1,2-isopropylidenedioxycyclohexadienes. Journal of the Chemical Society. Perkin Transactions. i (5): 1255-1263, 1991

Research on microbial oxidation of benzene. I. Determination & chemistry of benzene reduction. Archiv für Mikrobiologie 28(4): 383-393, 1958

Microbial oxidation in synthesis preparation of myo inositol phosphates and related cyclitol derivatives from benzene. Tetrahedron 46(13-14): 4995-5026, 1990

Microbial oxidation in synthesis preparation from benzene of the cellular secondary messenger myo inositol 1 4 5 trisphosphate ip 3 and related derivatives. Tetrahedron Letters 29(41): 5305-5308, 1988

Novel oxidation chemistry of catecholamine derivatives and related compounds. Reddy, C C , G A Hamilton And K M Madyastha (Ed ) Biological Oxidation Systems, Vols 1 And 2; Symposium, Bangalore, India, October 22-26, 1989 Xxi+534p (Vol 1); Xx+535p (Vol 2) Academic Press, Inc : San Diego, California, Usa; London, England, Uk Illus 347-364, 1990

Acyl C-O bond cleavage in Cp2*TiCOR compounds: formation of benzene derivatives by Cp*-ring expansion involving incorporation of the acyl carbon atom (Cp*=η5-C5Me5). Journal of Organometallic Chemistry 320(3): 289-293, 1987

Research on microbial oxidation of benzene. II. Description & systematic position of benzene-reducing microorganisms. Archiv für Mikrobiologie 28(4): 394-403, 1958

Versuche zur Synthese eines formalen Nitriloxid-Addukts des Benzols. 1,3-Dipolare Cycloadditionen an Bicyclo[2.2.0]hex-5-en-2,3-dicarbonsäureanhydrid, Dewarbenzol und 1,4-Cyclohexadien - Essais de synthèse d'adduits de nitrile oxydes formels-benzène. Cycloadditions dipolaires 1,3 de l'anhydride bicyclo [2.2.0] hexène-5 dicarboxylique-2,3, du benzène de Dewar et du cyclohexadiène-1,4 - Experiments to synthetize a formal nitrile oxyde-benzene adduct. 1,3-Dipolar cycloadditions to b. Chemische Berichte 118(10): 4203-4223, 1985

Oxidation of organic substances by tervalent manganese compounds: VIII. Determination of benzene polyhydroxy and aminohydroxy derivatives with a standard solution of hexaquomanganese(III) ion in perchloric acid. Microchemical Journal 22(4): 484-488, 1977

Studies in the chemistry of poly halogeno benzene compounds the synthesis and reactivity of 2 3 5 6 tetra chloro benzene sulfonyl chlorides and 2 3 4 5 tetra chloro benzene sulfonyl chlorides and related compounds. Australian Journal of Chemistry 29(7): 1573-1582, 1976

Factors influencing the relative tendencies for ortho and meta cycloadditions of ethylenic compounds to the benzene ring. Tetrahedron (Oxford. Print) 42(21): 6011-6014, 1986

Stereoselective Intramolecular Oxime Olefin Cycloadditions Involving Carbohydrate Derived Precursors. Synlett 1998(12): 1333-1334, 1998

Rh(I)-catalyzed formal [2+2+2] cycloadditions of 1,6-diynes with potassium (Z)-(2-bromovinyl)trifluoroborate: a new strategy and a facile entry to polysubstituented benzene derivatives. Chemical Communications 46(21): 3800-3802, 2010

The Game of Electrons: Organocatalytic Higher-Order Cycloadditions Involving Fulvene- and Tropone-Derived Systems. Chemistry 26(10): 2120-2132, 2020

New 2-pyridone derivatives via 1,3-dipolar cycloadditions of novel mesoionic compounds. Journal of Organic Chemistry 52(8): 1599-1601, 1987