Diazomethane

Boer, J. de; Backer, H. J.

doi:10.1002/0471264180.os036.07

Cited by 27 publications

(40 citation statements)

References 7 publications

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“…Trimethylsilyl chloride (TMSCl), pyridine, and triethylamine (NEt 3 ) were distilled from sodium hydride immediately prior to use. Sodium iodide was dried by heating at 90 °C (2 torr) for 12 h. TEMPO + BF 4 − , 14 p -acetamidobenzenesulfonyl azide ( p ABSA), TsN 3 , 26 bis( N - tert -butylsalicylaldehydiminato) copper (II, Cu(tbs) 2 ), 27 Dess-Martin periodinane (DMP), 28 diazomethane, 29 and Amberlyst A26 (S 2 O 3 2− ) 30 were prepared by known methods. Other reagents were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization–Cope or Cyclopropanation–Cope Rearrangements as Key Steps

et al. 2017

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Recently, we reported a convergent cyclopropanation-Cope approach to the core of ineleganolide, which was the first disclosed synthesis of the core of the norditerpene natural product ineleganolide. In this complementary work, a model system for the core of ineleganolide has been prepared through a series of tandem cyclopropanation-Cope and translactonization-Cope rearrangements. Work with this model system has enriched our understanding of the cyclopropanation-Cope rearrangement sequence. Additionally, research into this model system has driven the development of tandem translactonization-Cope rearrangements.

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Section: Methodsmentioning

confidence: 99%

Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization–Cope or Cyclopropanation–Cope Rearrangements as Key Steps

et al. 2017

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“…Common methods include (i) diazo transfer, 58,59 (ii) diazotization, 60,61 (iii) hydrazone decomposition 62,63 or hydrazone oxidation, 64,65 (iv) rearrangement of N -alkyl N -nitroso compounds, 8,66 (v) 1,3-disubstituted acyl (or aryl) triazine fragmentation, 67,68 and (vi) elaboration of other diazo compounds (Figure 2). 69–73 Most of these routes have been reviewed extensively for their merits in the context of synthetic chemistry.…”

Section: Preparationmentioning

confidence: 99%

“…Diazomethane and other diazoalkanes are, however, highly toxic 5–7 and explosively reactive, 8,9 and have little utility in the context of chemical biology. The problem arises from their high basicity, as protonation of the α carbon of a diazo group leads to the formation of a diazonium species (R 1 R 2 HC–N 2 + ) poised for a rapid S N 2 reaction that releases nitrogen gas.…”

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confidence: 99%

Diazo Compounds: Versatile Tools for Chemical Biology

2016

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Diazo groups have broad and tunable reactivity. That and other attributes endow diazo compounds with the potential to be valuable reagents for chemical biologists. The presence of diazo groups in natural products underscores their metabolic stability and anticipates their utility in a biological context. The chemoselectivity of diazo groups, even in the presence of azido groups, presents many opportunities. Already, diazo compounds have served as chemical probes and elicited novel modifications of proteins and nucleic acids. Here, we review advances that have facilitated the chemical synthesis of diazo compounds, and we highlight applications of diazo compounds in the detection and modification of biomolecules.

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“…The temperature program was : 5 min at 80-300°C at 10°min )1 . Extracts were analysed again after derivatization with diazomethane (formation of methyl derivatives), as described by De Boer & Backer (1956).…”

Section: Chemical Analysis and Identification Of Metabolitesmentioning

confidence: 99%