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The previously reported active Lewis pair (ALP)   i  Bu 2 Al–N(2-Ad)NC 5 H 10  ( 1 ) (2-Ad = 2-adamantyl) is readily accessible by hydroalumination of the hydrazone H 10 C 5 N–N=(2-C 10 H 14 ) with H–Al  i  Bu 2 . Treatment of  1  with two equivalents of isocyanates R-N=C=O yields six-membered AlC 2 N 2 O heterocycles  2  ( 2a , R = Ph;  2b , R =  p -Tol) by dual insertion into the Al–N bonds.  2a  reacts as a nucleophile with carboxylic acid chlorides R-C(O)–Cl [R = CH 2   t  Bu,  p -Tol, H 2 CCH(Me)C 6 H 4 (4-CH 2 CHMe 2 ) (Ibu-profen acid chloride), 0.5 (1,4-C 6 H 4 )] to afford by elimination of   i  Bu 2 AlCl and hydrolysis new triuret derivatives R-C(O)[N(Ph)C(O)] 2 –N(2-Ad)NC 5 H 10  ( 3a  to  3d ) as colourless, sparingly soluble solids in moderate ( 3c ) to high ( 3b ) yields. The analogous reaction of  2a  with ( p -Tol)–C(Cl)=N( p -Tol) leads to the imidoyl derivative ( p -Tol)N=C( p -Tol)[N(Ph)C(O)] 2 –N(2-Ad)NC 5 H 10  ( 4a ), which showed a fast exchange of phenyl and tolyl groups to yield a mixture of isomers. The analogous reaction of  2b  affords the corresponding compound  4b  for which a single isomer is isolated despite the scrambling of substituents.

zeitschrift für naturforschung b

Al/N-based active Lewis pairs: isocyanate insertion products as efficient nucleophiles employed for the facile generation of highly functional molecules