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Bor-stabilisierte Carbene, III [3 + 2]-Cycloadditionen an Borio-Nitrilylide / Boron-Stabilized Carbenes, III [3 + 2]-Cycloadditions to Borio Nitrile Ylides
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The borio nitrile ylides Li[Ph3B—C =N—CH—R] (R = CO2Et, Tos) react with various dipolarophiles regio- and site-specifically to give boron complexes of carbenoid five-membered heterocycles which have been alkylated in order to accomplish their isolation. Thus, isocyanates and isothiocyanates/trialkyloxonium salts give rise to the imidazoline-2-ylidene complexes 2-5, CS2/Et3O+ to the thiazoline-2-ylidene complex 6 and acetone/Et3O+ to the oxazoline-2-ylidene complexes 7a,b. Aryldiazonium ions are added regiospecifically in the “wrong” orientation that leads to mesoionic 1,2,4-triazolium-3-ato-triphenylborate complexes (11a— e). The spectroscopic properties of the new complexes are discussed. Of (1-phenyl-4 H- 5-carbethoxy-triazolium-3-ato)triphenylborate (11a) an X-ray structure analysis has been carried out.
Walter de Gruyter GmbH
Title: Bor-stabilisierte Carbene, III [3 + 2]-Cycloadditionen an Borio-Nitrilylide / Boron-Stabilized Carbenes, III [3 + 2]-Cycloadditions to Borio Nitrile Ylides
Description:
The borio nitrile ylides Li[Ph3B—C =N—CH—R] (R = CO2Et, Tos) react with various dipolarophiles regio- and site-specifically to give boron complexes of carbenoid five-membered heterocycles which have been alkylated in order to accomplish their isolation.
Thus, isocyanates and isothiocyanates/trialkyloxonium salts give rise to the imidazoline-2-ylidene complexes 2-5, CS2/Et3O+ to the thiazoline-2-ylidene complex 6 and acetone/Et3O+ to the oxazoline-2-ylidene complexes 7a,b.
Aryldiazonium ions are added regiospecifically in the “wrong” orientation that leads to mesoionic 1,2,4-triazolium-3-ato-triphenylborate complexes (11a— e).
The spectroscopic properties of the new complexes are discussed.
Of (1-phenyl-4 H- 5-carbethoxy-triazolium-3-ato)triphenylborate (11a) an X-ray structure analysis has been carried out.
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