om960449u_si_001.pdf (1.16 MB)
Download fileSynthesis and Reactions of a Stannanethione Derived from a Kinetically Stabilized Diarylstannylene
journal contribution
posted on 1996-10-15, 00:00 authored by Masaichi Saito, Norihiro Tokitoh, Renji OkazakiStannanethione Tbt(Tip)SnS (Tbt =
2,4,6-tris[bis(trimethylsilyl)methyl]phenyl; Tip
=
2,4,6-triisopropylphenyl), containing a novel tin−sulfur double bond,
was synthesized by
the reactions of the corresponding kinetically stabilized
diarylstannylene Tbt(Tip)Sn: with
styrene episulfide or elemental sulfur. An absorption maximum due
to the n−π* transition
of the tin−sulfur double bond appeared at 473 nm in hexane. It
reacted with thiocumulenes
such as carbon disulfide and phenyl isothiocyanate and with styrene
oxide and mesitonitrile
oxide to give the corresponding cycloadducts. The structure of the
[2 + 2] cycloadduct of a
stannanethione with carbon disulfide was determined by X-ray structural
analysis. In
contrast to Tbt(Tip)SnS, the less hindered stannanethione
Tbt(Mes)SnS (Mes = mesityl)
dimerized at room temperature to afford the corresponding
1,3,2,4-dithiadistannetane.