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・ Pyrodictium
・ Pyrodictium abyssi
・ Pyrodinium bahamense
・ Pyroeis
・ Pyroelectric crystal
・ Pyroelectric fusion
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・ Pyrogallol 1,2-oxygenase
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Pyridyne
・ Pyrilampes
・ Pyrilia
・ Pyrimethamine
・ Pyrimethanil
・ Pyrimidine
・ Pyrimidine analogue
・ Pyrimidine dimer
・ Pyrimidine metabolism
・ Pyrimidine oxygenase
・ Pyrimidine phosphorylase
・ Pyrimidine-5'-nucleotide nucleosidase
・ Pyrimidine-deoxynucleoside 1'-dioxygenase
・ Pyrimidine-deoxynucleoside 2'-dioxygenase
・ Pyrimidine-nucleoside phosphorylase


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Pyridyne : ウィキペディア英語版
Pyridyne
Pyridyne in chemistry is the pyridine analogue of benzyne.〔''Handbook of Heterocyclic Chemistry'', (2010) y, Alan R. Katritzky,Christopher A. Ramsden,J. Joule,Viktor V. Zhdankin〕 This reactive intermediate is of some importance to scientific research. Pyridynes are the class of compounds sharing the pyridyne building motive. Two isomers exist, the 2,3-pyridine (2,3-didehydropyridine) and the 3,4-pyridyne (3,4-didehydropyridine). The reaction of 3-bromo-4-chloropyridine with furan and lithium amalgam gives 1,4-epoxy-dihydroquinoline through the 2,3-pyridyne intermediate. The reaction of 4-bromopyridine with sodium in liquid ammonia gives both 3-aminopyridine and 4-aminopyridine through the 3,4-pyridyne intermediate and an E1cB-elimination reaction.〔Heterocyclic Chemistry, (2001) Malcolm Sainsbury〕
==History==
Pyridynes were first postulated by Levine and Leake in 1955.〔''Rearrangement in the Reaction of 3-Bromopyridine with Sodium Amide and Sodioacetophenone'' ROBERT LEVINE and WILLIAM W. LEAKE Science 27 May 1955: Vol. 121 no. 3152 p. 780 〕 In 1969 Zoltewicz and Nisi trapped 3,4-pyridyne in a reaction of 3-bromopyridine with methylmercaptan and sodium amide in ammonia. The methylthio and amino pyridines were found to be formed in the same ratio.〔''Trapping of 3,4-pyridyne by thiomethoxide ion in ammonia'' John A. Zoltewicz and Carlo Nisi The Journal of Organic Chemistry 1969 34 (3), 765-766〕
:
In 1972 Kramer and Berry inferred the formation of 3,4-pyridyne in gas-phase photolysis of pyridine-3-diazonium-4-carboxylate via time-of-flight mass spectrometry. The dimer compound diazabiphenylene was detected.〔''Gaseous 3,4-pyridyne and the formation of diazabiphenylene'' Jerry Kramer and R. Stephen Berry Journal of the American Chemical Society 1972 94 (24), 8336-8347 〕 In 1988 Nam and Leroy reported the matrix isolation (13K, Ar) of 3,4-pyridyne by photolysis of 3,4-pyridinedicarboxylic anhydride with the IR-spectrum revealing an acetylenic bond in the same way as ortho-benzyne.

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