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[( N ‐Lithio‐ N ‐mesitylsulfonyloxy‐ tert ‐butylcarbamate) 2 ·(thf) 3 ]: Crystal Structure of a Nitrenoid
Author(s) -
Boche Gernot,
Boie Christiane,
Bosold Ferdinand,
Harms Klaus,
Marsch Michael
Publication year - 1994
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.199401151
Subject(s) - nucleophile , crystal structure , molecule , dimer , crystallography , chemistry , solid state , crystal (programming language) , stereochemistry , catalysis , organic chemistry , computer science , programming language
The NO bond in 1 lengthens by roughly 6 pm when the neutral compound (X = H) is N‐lithiated (X = Li). This key result of the first crystal structure analysis of a nitrenoid explains the facile replacement of the OR groups in nitrenoids R 1 (Li)OR 2 by nucleophiles like R'Li and is in accord with calculational predictions. In the solid state 1 (X = Li) occurs as a Li‐linked dimer with three Li‐coordinating THF molecules, one of which bridges the two Li centers. R = 2,4,6‐trimethylphenyl.
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