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Hydrated oxocarbons, IV. Silylation of 1,1‐dihydroxy compounds
Author(s) -
Yalpani Mohamed,
Wilke Günther
Publication year - 1985
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.19851180225
Subject(s) - chemistry , silylation , hexamethyldisiloxane , geminal , ninhydrin , alkylation , organic chemistry , reagent , trimethylsilyl , cyclohexane , medicinal chemistry , pyrolysis , catalysis , biochemistry , physics , plasma , amino acid , quantum mechanics
The action of various silylating agents on mono‐ and polyvicinal 1,1‐dihydroxy compounds has been investigated. Some of these reagents converted ninhydrin ( 2 ) and rhodizonic acid ( 17 ) into the corresponding geminal bis(trimethylsilyloxy) derivatives 1 and 20 , respectively. Compound 1 readily fragments to form hexamethyldisiloxane and indantrione ( 4 ). The rhodizonic acid derivative 20 is, however, rather stable and even on pyrolysis at 500°C gives only traces of the tetraketone 21 . With other silylating agents unexpected C ‐alkylation or C ‐amidation at the dihydroxy carbon is observed. Silylation of perhydroxycyclobutane and ‐cyclohexane leads to ring opened and contracted products.