Reaction of 1,1‐Dimethylsilene with Formaldehyde | Zendy

Trommer Martin | Zendy; Sander Wolfram | Zendy; Ottosson CarlHenrik | Zendy; Cremer Dieter | Zendy

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Reaction of 1,1‐Dimethylsilene with Formaldehyde

Author(s) -

Trommer Martin,

Sander Wolfram,

Ottosson CarlHenrik,

Cremer Dieter

Publication year - 1995

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199509291

Subject(s) - diradical , formaldehyde , singlet state , carbene , photochemistry , chemistry , silylation , aldehyde , silence , van der waals force , medicinal chemistry , computational chemistry , organic chemistry , catalysis , molecule , physics , atomic physics , excited state , acoustics

Even at 30 K 1,1‐dimethylsilene ( 1 ) reacts smoothly with formaldehyde in a thermal transformation to give trimethylsiloxycarbene ( 2 ). This singlet carbene is extremely photolabile and rapidly rearranges on irradiation with visible light (λ > 570 nm) in a 1,2 migration of the silyl group to give aldehyde 3 . According to CCSD(T)/6‐31G(d,p) calculations on the parent silence, reaction takes place via a van der Waals complex and a diradical intermediate.

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