Reactions with Diazoalkanes. V. Action of Diazoalkanes and of Aryl Azides on N-Arylmaleimides

Mustafa, Ahmed; Zayed, S. M. A. D.; Khattab, Samir A.

doi:10.1021/ja01582a041

Cited by 54 publications

(12 citation statements)

References 2 publications

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“…The sparse solubility of the pyrazoline solids 13 is in stark contrast to the previous report of 13d, which describes its solubility in chloroform. 20 The reported melting point of 143°also does not agree with our findings, which revealed decomposition for the white precipiate 13d at ca. 151°before melting.…”

Section: Preparation and Characterization Of Crystalline Pyrazolinescontrasting

confidence: 90%

Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes

Shiraki

Vogelsberg

2012

Photochem Photobiol Sci

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To expand on the limited number of examples that exist in the literature for the solid-state photodenitrogenation of azoalkanes, a series of crystalline 7-alkyl-2,3,7-triazabicyclo[3.3.0]oct-2-ene-6,8-diones with varying 4,4-substituents were prepared. Their photochemical behavior in solution and in the solid state was dependent on the 4,4-substitution of the 1-pyrazoline ring, with unsubstituted pyrazoline giving a mixture of products both in solution and in the solid state. Diphenyl substituted pyrazolines denitrogenate spontaneously in solution but require light exposure to react quantitatively in the solid state. t-Butyl-phenyl substituted pyrazolines were shown to denitrogenate both chemo- and diastereoselectively in solution and in the solid state to yield a single product in quantitative yield.

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Section: Preparation and Characterization Of Crystalline Pyrazolinescontrasting

confidence: 90%

Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes

Shiraki

Vogelsberg

2012

Photochem Photobiol Sci

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“…Further recrystallization from EtOAc gave the syn-anti-oxime isomers 6a, mp 126M27 °C, and 6b, mp 132-133 °C. Spectral properties: IR (6a) 3200-2100, 1642, 1590.1131.1030.1010.732.712.692.673.630 cm"1; IR (6b) 3200-2100, 1659,1590,1510,1418,1340,1265,1131,1027,1008, 758, 738, 714,691, 675.630 cm'1; MS m/e (rel intensity) 237 (0.2), 219 (6), 206 (29), 177 (8), 165 (7), 130 (10), 114 (4), 106 (100), 78 (97), 73 (49), 51 (40), 42 (45), identical for 6a and 6b; NMR (mixture of 6a and 6b) (CDCI3) 9.42-7.25 (4 H, m, pyridyl CH), 4.48 (1.8 H, t, CH3NN=0, 6a + 6b E isomers), 3.81 (0.5 H, m, -CH2N(N=0)CH3, 6a + 6b Z isomers), 3.21 (2 H, t, HON=CCH2-), 3.15 ppm (2.7 H, s, CH3NN=0, 6a + 6b E isomers). Anal.…”

Section: Methodsmentioning

confidence: 99%

Chemical studies on tobacco smoke. 52. Reaction of nicotine and sodium nitrite: formation of nitrosamines and fragmentation of the pyrrolidine ring

Hecht¹,

Chen²,

Ornaf³

et al. 1978

J. Org. Chem.

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“…Formation of the trans-diester (7) was preceded by an isomerization of the azomethine ylide cis-dicarboxylate to the trans-dicarboxylate [3J.…”

Section: Configuration Of a Cis-disubstituted Azomethine Ylidementioning

confidence: 99%

Configuration of a cis‐Disubstituted Azomethine Ylide

Huisgen¹,

Mäder²

1969

Angew. Chem. Int. Ed. Engl.

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In azomethine oxides (nitrones) the oxygen stabilizes the pegative charge better than the carbon of the carbanion in Dipolarophile a = b Tetracyanoethylene Dimethyl Diethyl acetylenedicarboxylate azodicarboxylate Diethyl mesoxalate Dimethyl fumarate Tetraethyl ethylenetetracarboxylate Norbornene Cyclohexene Phenanthrene Table 1. r r n s -( l ) [via cis-(2)1 with dipolarophiles at IW-140 "C [a]. Steric course of some reactions of cis-jl) [via trans-(2)l and From &-(I) [bl (3). yield ( %) 88 98 96 94 100 99 86 78 azomethine ylides. This is responsible for the conversion of oxaziranes into the open-chain nitrones.

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Reactions with Diazoalkanes. V. Action of Diazoalkanes and of Aryl Azides on N-Arylmaleimides

Cited by 54 publications

References 2 publications

Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes

Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes

Chemical studies on tobacco smoke. 52. Reaction of nicotine and sodium nitrite: formation of nitrosamines and fragmentation of the pyrrolidine ring

Configuration of a cis‐Disubstituted Azomethine Ylide

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