The preparation and reactivity of some photoactivable reactive dyes

Braybrook, David R.; Moloney, Mark G.; Osborn, Helen M. I.; Norris, William J.

doi:10.1016/1010-6030(93)85038-a

Journal of Photochemistry and Photobiology A: Chemistry

1993

DOI: 10.1016/1010-6030(93)85038-a

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The preparation and reactivity of some photoactivable reactive dyes

David R. Braybrook

Mark G. Moloney

Helen M. I. Osborn

et al.

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Cited by 8 publications

(1 citation statement)

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“…The C=N bands appear at 1690-1650cm-' [30] [31]. The UV spectra show a characteristic absorption between 210 and 215 nm for the n-m* transition [32]. In the 'H-NMR spectra, the signals of NH-SO, at 7.71-7.55 ppm indicate the (Z)-configuration [I81 [31] [33] [34].…”

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Glycosylidene Carbenes. Part 21. Synthesis of N‐tosylglycono‐1,4‐lactone hydrazones as precursors of glycofuranosylidene carbenes

Mangholz

Vasella

1995

Helvetica Chimica Acta

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The W -(glycofuranosylidene)toluene-4-sulfonohydrazides 5 and 10 (Scheme I ) were prepared in good yields by oxidation (1,3-dibromo-5,5-dimethylhydantoin/Et3N) of the W -glycosyltoluene-4-sulfonohydrazides 4 and 9, which were obtained from 2,3,5-tri-0-benzyl-o-ribose (3) and 2,3,5-tri-O-benzyI-o-arabinos.e (8), respectively, and toluene-4-sulfonohydrazide. The analogous naphthalene-2-sulfonohydrazides 7 and 12 were similarly prepared from 3 and 8 via 6 and 11. Photolysis in the presence of phenol of the sodium salt 15 (Scheme 2), best generated in situ, yielded the anomeric glycosides 16, some 5, and traces of the glycosides ( Introduction. -Glycopyranosylidene carbenes, known reactive intermediates [ 11, are best generated from diazirines, such as 1, under mild thermal and photochemical conditions [2]. They are also formed from the alkali salts of N'-glycosylidenesulfonohydrazides, such as 2 [3] [4], or (in low yields) from diazides under photochemical conditions [5]. N' -(Glycopyranosylidene)sulfonohydrazides are more readily prepared than the corresponding diazirines and are more stable. Their salts react similarly to diazirines in forming glycosides with phenols [&9] and cyclopropanes with electron-deficient alkenes [3] [9] [lo]. Thermolysis of N' -(glycopyranosylidene)sulfonohydrazides, however, also generates sulfinates, and this results in the formation of additional by-products [I 11 [12].

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Glycosylidene Carbenes. Part 21. Synthesis of N‐tosylglycono‐1,4‐lactone hydrazones as precursors of glycofuranosylidene carbenes

Mangholz

Vasella

1995

Helvetica Chimica Acta

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Post‐Polymerization Modification of Materials using Diaryldiazomethanes: Changes to Surface Macroscopic Properties

Bagwell

Leonard

Griffiths

et al. 2013

Macro Reaction Engineering

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Direct introduction of phosphonate by the surface modification of polymers enhances biocompatibility

Choong

Griffiths

Moloney

et al. 2009

Reactive and Functional Polymers

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The preparation and reactivity of some photoactivable reactive dyes

Cited by 8 publications

References 28 publications

Glycosylidene Carbenes. Part 21. Synthesis of N‐tosylglycono‐1,4‐lactone hydrazones as precursors of glycofuranosylidene carbenes

Glycosylidene Carbenes. Part 21. Synthesis of N‐tosylglycono‐1,4‐lactone hydrazones as precursors of glycofuranosylidene carbenes

Post‐Polymerization Modification of Materials using Diaryldiazomethanes: Changes to Surface Macroscopic Properties

Direct introduction of phosphonate by the surface modification of polymers enhances biocompatibility

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