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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
Author(s) -
Pless Janos
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590216
Subject(s) - chemistry , amine gas treating , protecting group , hydrogen bromide , bromide , group (periodic table) , acetic acid , hydrogen bond , medicinal chemistry , amino acid , peptide , stereochemistry , organic chemistry , molecule , alkyl , biochemistry , bromine
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):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.