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Struktur und Chemie von tautomeriefähigen Heterocyclen, II. Trimethylsilylierung von Diethylmalonohydrazid und seinen Monomethyl‐Derivaten. NMR‐Spektroskopische Strukturuntersuchung der Produkte
Author(s) -
Steigel Alois
Publication year - 1980
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.19801131224
Subject(s) - chemistry , triethylamine , silylation , tautomer , trimethylsilyl , lactam , medicinal chemistry , stereochemistry , nuclear magnetic resonance spectroscopy , derivative (finance) , catalysis , organic chemistry , financial economics , economics
Structure and Chemistry of Heterocycles Capable of Tautomerism, II. Trimethylsilylation of Diethylmalonohydrazide and its Monomethyl Derivatives. NMR Spectroscopic Study of the Structure of the Products The trimethylsilylation of diethylmalonohydrazide ( 2 ) and its monomethyl derivatives 3 and 4 yields silyl compounds which only exist in the lactam‐lactim form. While the trimethylsilylation of 2 with two equivalents of chlorotrimethylsilane and two equivalents of triethylamine gives the N , O ‐disilyl derivative 6 , the use of one equivalent of each affords the O ‐silyl compound 5 in pure state. 5 is also formed in the reaction of 6 with 2 by catalysis with triethylamine. The lactam‐lactim structure of 5 and 6 as well as of the trimethylsilyl derivatives 7 and 8 of the isomeric compounds 3 and 4 , respectively, is established by 1 H, 13 C, and 29 Si NMR spectroscopy.