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Synthesis and Structural Characterization of Azatitanacyclobutane Derivatives
Author(s) -
Beckhaus Rüdiger,
Wagner Martin,
Wang Ruimin
Publication year - 1998
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199802)1998:2<253::aid-ejic253>3.0.co;2-x
Subject(s) - chemistry , cycloaddition , aniline , reactivity (psychology) , ring (chemistry) , medicinal chemistry , hexane , stereochemistry , chlorine atom , organic chemistry , catalysis , medicine , alternative medicine , pathology
The titanocene vinylidene intermediate [Cp* 2 Ti=C=CH 2 ] ( 9 ) reacted with the carbodiimides R−N=C=N−R [R = p ‐CH 3 C 6 H 4 ( 19a ), C 6 H 11 ( 19b )] to give the N=C‐cycloaddition products [Cp* 2 Ti{−NR−C(=NR)−(C=CH 2 )−}] [(R = p ‐CH 3 C 6 H 4 ( 20a ), C 6 H 11 ( 20b )]. The X‐ray structure of 20a in form of a surprisingly stable n ‐hexane clathrate is presented. The azatitanacyclobutane [Cp* 2 Ti{−NPh−C(Ph)(H)−(C=CH 2 )−}] ( 22 ) was formed from the reaction between 9 and benzylidene aniline [PhN=C(Ph)H ( 21 )]. Reactivity studies showed that azatitanacyclobutanes are unreactive upon typical ring‐enlargement reactions as observed for other four‐membered titanacycles.