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A photolabile protection strategy for terminal alkynes

Tina Gschneidtner (Institutionen för kemi- och bioteknik, Polymerteknologi) ; Kasper Moth-Poulsen (Institutionen för kemi- och bioteknik, Polymerteknologi)
Tetrahedron Letters (0040-4039). Vol. 54 (2013), 40, p. 5426-5429.
[Artikel, refereegranskad vetenskaplig]

We present a strategy for photolabile protection of terminal alkynes. Several photo-caged alcohols were synthesized via mild copper(II)-catalyzed substitution between tertiary propargylic alcohols and 2-nitrobenzyl alcohol to build up robust, base stable o-nitrobenzyl (NB) photo-cleavable compounds. We compare the new photolabile protecting group with the commonly used alkyne protecting group, 2-methyl-3-butyn-2-ol and the results show that NB ethers are stable under the cleaving conditions for the cleavage of methylbutynol protected alkynes. Additionally, we present the synthesis of photo-cleavable NB derivatives containing thiol groups that can serve as agents for photoinduced surface functionalization reactions.

Nyckelord: Photolabile protection, Terminal alkynes, o-Nitrobenzyl, diels-alder reactions, reaction-mechanisms, propargylic alcohols, p-hydroxyphenacyl, click chemistry, substitution, derivatives, photolysis, surfaces, phototrigger, dor spa, 1993, nature, v364, p555



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Denna post skapades 2013-10-28. Senast ändrad 2014-09-02.
CPL Pubid: 185734

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Polymerteknologi (2005-2014)

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Materialvetenskap
Organisk kemi

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