Photolysis of N-phenylhydroxylamine: a novel photochemical disproportionation reaction in N-O bond cleavage assisted by hydrogen bonding

被引：7

作者：

White, RC ^{[1
]}

Selvam, T

Ihmels, H

Adam, W

机构：

[1] Sam Houston State Univ, Dept Chem, Huntsville, TX 77341 USA

[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 1999年 / 122卷 / 01期

关键词：

photolysis; N-phenylhydroxylamine; hydrogen bonding; azobenzene;

D O I：

10.1016/S1010-6030(99)00019-2

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The photochemistry of N-phenylhydroxylamine (9) has been examined in the solution phase and in the solid state. The major products are aniline and nitrosobenzene. The nitrosobenzene quickly reacts with 9 to generate azoxybenzene and with aniline to produce azobenzene. The quantum yields for the disappearance of 9 are reasonably high (0.25-0.29) and suggest that the photochemical reactions proceed from a hydrogen-bonded dimer. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：7 / 10

页数：4

共 50 条

[21] HETEROCYCLIC SYNTHESIS BY π-ACIDIC METAL CATALYZED REACTIONS VIA N-O BOND CLEAVAGE
Nakamura, Itaru
Terada, Masahiro
HETEROCYCLES, 2014, 89 (04) : 845 - 868
[22] PHOTOCHEMICAL BEHAVIOR OF CYCLIC IMINO ETHERS - THE N-O BOND FISSION, SYN-ANTI ISOMERIZATION AND CYCLOADDITION REACTIONS IN THE C=N-O CHROMOPHORE
MUKAI, T
KUMAGAI, T
SAIKI, H
KAWAMURA, Y
JOURNAL OF PHOTOCHEMISTRY, 1981, 17 (1-2): : 116 - 116
[23] METAL CARBONYL-INDUCED N-O BOND-CLEAVAGE OF THE OXIME GROUP
NITTA, M
IINO, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (07) : 2365 - 2367
[24] Bond energy/bond order relationships for N-O linkages and a quantitative measure of ionicity: the role of nitro groups in hydrogen-bonding
Johnstone, Robert A. W.
Loureiro, Rui M. S.
Cristiano, M. Lurdes S.
Labat, Gael
ARKIVOC, 2010, : 142 - 169
[25] Reductive cleavage of the N-O bond: elemental sulfur-mediated conversion of N-alkoxyamides to amides
Wang, Senlin
Zhao, Xue
Zhang-Negrerie, Daisy
Du, Yunfei
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (03) : 347 - 351
[26] Development of New Reactions Driven by N-O Bond Cleavage: from O -Acyl Hydroxylamines to Tetrodotoxin
Robins, Jacob G.
Johnson, Jeffrey S.
SYNLETT, 2023, 34 (13) : 1563 - 1572
[27] Sequential N-O and N-N Bond Cleavage of N-Heterocyclic Carbene-Activated Nitrous Oxide with a Vanadium Complex
Tskhovrebov, Alexander G.
Solari, Euro
Wodrich, Matthew D.
Scopelliti, Rosario
Severin, Kay
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) : 1471 - 1473
[28] Ru-Catalyzed Redox-Neutral Cleavage of the N-O Bond in Isoxazolidines: Isatogens to Pseudoindoxyls via a One-Pot [3+2]-Cycloaddition/N-O Cleavage
Kumar, Chepuri V. Suneel
Ramana, Chepuri V.
ORGANIC LETTERS, 2015, 17 (12) : 2870 - 2873
[29] Synthesis of Nonnatural Helical Polypeptide via Asymmetric Polymerization and Reductive Cleavage of N-O Bond
Ishido, Yuki
Kanbayashi, Naoya
Okamura, Taka-aki
Onitsuka, Kiyotaka
MACROMOLECULES, 2017, 50 (14) : 5301 - 5307
[30] Copper-Catalyzed N-N Bond Formation by Homocoupling of Ketoximes via N-O Bond Cleavage: Facile, Mild, and Efficient Synthesis of Azines
Zhao, Mi-Na
Liang, Hao
Ren, Zhi-Hui
Guan, Zheng-Hui
SYNTHESIS-STUTTGART, 2012, 44 (10): : 1501 - 1506

← 1 2 3 4 5 →