Eigenschaften und Verwendbarkeit des 10, 11‐Dihydro‐5 H ‐dibenzo[ a,d ]cyclohepten‐5‐yl‐Rests (= 5‐Dibenzosuberyl‐Rests) als neue Schutzgruppe für Amine, Aminosäuren, Alkohole, Thiole und Carbonsäuren

Properties and suitability of the 10,11‐dihydro‐5 H ‐dibenzo[ a, d ]cyclohepten‐5‐yl group (= 5‐dibenzosuberyl group) as a new protecting group for amines, amino‐acids, alcohols, thiols and carboxylic acids. The 10,11‐dihydro‐5 H ‐dibenzo[ a,d ]cyclohepten‐5‐yl group (5‐dibenzosuberyl group): magnif...

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Veröffentlicht in:Helvetica chimica acta 1976-03, Vol.59 (2), p.499-512
1. Verfasser: Pless, Janos
Format: Artikel
Sprache:eng
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Zusammenfassung:Properties and suitability of the 10,11‐dihydro‐5 H ‐dibenzo[ a, d ]cyclohepten‐5‐yl group (= 5‐dibenzosuberyl group) as a new protecting group for amines, amino‐acids, alcohols, thiols and carboxylic acids. The 10,11‐dihydro‐5 H ‐dibenzo[ a,d ]cyclohepten‐5‐yl group (5‐dibenzosuberyl group): magnified image has been found useful for protecting amines, alcohols, thiols, and carboxylic acids. Furthermore, the investigated 5‐amino compounds are extremely stable in strongly acidic media ( e. g. in hydrogen bromide) and still the amino group is easily cleaved under mild conditions, such as those used for N‐trityl compounds ( e.g. boiling in dilute acetic acid or catalytic hydrogenation). Hence this ring system could be a valuable and adaptable protecting group, especially in peptide chemistry.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19760590216