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The reaction of [ i Pr 2 N=CHCl]Cl with 2-phenylbenzthiazolidine (Ph-BtzH) and subsequent anion metathesis afforded the formamidinium salt [(Ph-Btz)CH(N i Pr 2 )][PF 6 ] ([ 1a H][PF 6 ]). The reaction of [ 1a H][PF 6 ] with (Me 3 Si) 2 NNa in the presence of grey selenium furnished the selenourea derivative  1a Se as trapping product of the acyclic diaminocarbene  1a . In the absence of selenium, a 2 H -1,4-benzothiazine derivative ( 2 ) was obtained, which is an isomer of  1a , whose formation is plausibly initiated by deprotonation of [ 1a H] +  not at the cationic N 2 CH unit, but at the neighbouring PhCH position. CO was ineffective as trapping reagent for  1a . [ 1a H][PF 6 ],  1a Se and  2  have been structurally characterised by X-ray diffraction.

zeitschrift für naturforschung b

Evaluation of benzthiazolidine-based formamidinium salts for the synthesis of penem-type  β -lactams by uncatalysed carbonylation of acyclic diaminocarbenes