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Disiloxanes, Disilazanes and Related Compounds Derived from 1,8‐Disilynaphthalene
Author(s) -
Schröck Robert,
Dreihäupl KarlHeinz,
Sladek Alexander,
Angermaier Klaus,
Schmidbaur Hubert
Publication year - 1996
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.19961290505
Subject(s) - chemistry , triflic acid , silylation , trifluoromethanesulfonate , naphthalene , disiloxane , toluene , phosphonium , medicinal chemistry , tetrafluoroborate , molecule , organic chemistry , catalysis , ionic liquid
The synthesis, spectroscopic data and molecular structures of heterocycles derived from 1,8‐disilylnaphthalene are reported. The key intermediate for the preparation of the title compounds is 1,8‐bis[(trifluoromethylsulfonyl)silyl]naphthalene ( 3 ), which is prepared from 1,8‐bis[(4‐methoxyphenyl)silyl]naphthalene ( 2 ) by treatment with two equivalents of triflic acid in toluene at –20°C. The resulting silyl triflate is stable only below this temperature and was not isolated. Its reactions with water, ammonia, amines, and sulfane give the corresponding disiloxane, disilazanes and disilthiane. The molecular structure of Si,Si′ ‐(Naphthalene‐1,8‐diyl)‐ N ‐phenyldisilazane ( 8 ) was determined by X‐ray diffraction. Treatment of 2 with substoichiometric amounts of triflic acid and subsequent reaction of the resulting monosilyl triflate with tert ‐butylamine gives a related chiral N ‐tert‐butyl‐ Si ‐(4‐methoxyphenyl)disilazane 10 . Its molecular structure was proven by X‐ray diffraction. A cyclic phosphonium bis(silyl)methylide ( 11 ) was synthesized by a transylidation process using 3 and CH 2 =P(NMe 2 ) 3 . The structure of 11 was also determined by X‐ray diffraction.