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Polyine, 8. Zur Synthese von Amino‐ und Bisamino‐Vertretern des Octatetrains
Author(s) -
Faul Dieter,
Himbert Gerhard
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210726
Subject(s) - chemistry , morpholine , cyclohexanone , piperidine , lithium (medication) , cyanogen bromide , butyllithium , amine gas treating , organic chemistry , medicinal chemistry , catalysis , medicine , biochemistry , peptide sequence , gene , endocrinology
Polyynes, 8. ‐ Synthesis of Amino and Bisamino Derivatives of Octatetrayne The (7,8,8‐trichloro‐7‐octene‐1,3,5‐triynyl)amines 4a,b , formed by the reaction of the corresponding lithium 4‐aminobutadiynides 3 with perchlorobutenyne 1 , are dechlorinated by butyllithium to give the lithium 8‐aminooctatetraynides 5a,b . The latter react with chloromethyldiphenylsilane or with cyclohexanone to give the silylated and hydroxyalkylated compounds 6a,b and 7b , respectively. The unsymmetrically substituted octatetraynediamines 9a,b are obtained by treatment of the lithium compounds 5 with cyanogen bromide and by treatment of the formed bromoacetylenes 8 with piperidine or morpholine.