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Highly Efficient an...
Highly Efficient and Convenient Acid Catalyzed Hypersilyl Protection of Alcohols and Thiols by Tris(trimethylsilyl)silyl-N,N-dimethylmethaneamide
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- Alvi, Muhammad Rouf (författare)
- Uppsala universitet,Fysikalisk-organisk kemi
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- Jahn, Burkhard O. (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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- Tibbelin, Julius (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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visa fler...
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- Baumgartner, Judith (författare)
- Institut für Anorganische Chemie, Technische Universität Graz, Stremayrgasse 9, A-8010 Graz, Austria
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- Gómez, Cesar Pay, 1974- (författare)
- Uppsala universitet,Strukturkemi
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- Ottosson, Henrik (författare)
- Uppsala universitet,Fysikalisk-organisk kemi
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visa färre...
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(creator_code:org_t)
- 2012
- Engelska.
- Relaterad länk:
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https://urn.kb.se/re...
Abstract
Ämnesord
Stäng
- Tris(trimethylsilyl)silyl-N,N-dimethylmethaneamide, herein named hypersilylamide, is a convenient and efficient source of the hypersilyl group in the first widely applicable acid catalyzed protocol for silyl group protection of primary, secondary, tertiary alkyl as well as aryl alcohols and thiols in high yields. The sole by-product is N,N-dimethylformamide (DMF) and a range of solvents can be used, including DMF. A high selectivity in the protection of diols can be achieved, also for diols with very small differences in the steric demands at the two hydroxyl groups. Moreover, in the protection of equivalent alcohol and thiol sites the protection of the alcohol is faster, allowing for selective protection in high yields. Quantum chemical calculations at the M062X hybrid meta density functional theory level give insights on the mechanism for the catalytic process. Finally, the hypersilyl group is easily removed from all protected alcohols and thiols examined herein by irradiation at 254 nm.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Oorganisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Inorganic Chemistry (hsv//eng)
Nyckelord
- Chemistry with specialization in Inorganic Chemistry
- Kemi med inriktning mot oorganisk kemi
Publikations- och innehållstyp
- vet (ämneskategori)
- ovr (ämneskategori)