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Towards 2‐Silaallenes: Synthesis of Spirocyclic Precursors
Author(s) -
Goetze Brigitte,
Herrschaft Bernhard,
Auner Norbert
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030617
Subject(s) - norbornadiene , diphenylacetylene , chemistry , anthracene , reagent , reactive intermediate , molar ratio , crystal structure , stereochemistry , medicinal chemistry , crystallography , organic chemistry , catalysis
Reactions of dichlorodivinylsilane ( 2 ) and Li t Bu in a molar ratio 1/1 and 1/2 lead to highly reactive intermediates, which can be trapped by suitable reagents. In the presence of trimethylmethoxysilane, norbornadiene, anthracene and diphenylacetylene, products are formed that provide evidence for the intermediate formation of both the neopentylsilene H 2 C=CH(Cl)Si=CHCH 2 t Bu ( 3 ) and the 2‐silaallene t BuCH 2 CH=Si=CHCH 2 t Bu ( 4 ). The formation of double cycloadducts from 4 is particularly interesting as a preparatively facile route for the synthesis of silaspirocycles such as 13, 16 and 17 , which have been characterized by single‐crystal X‐ray structure analysis.