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

Abstract

Abstract The reaction of [iPr2N=CHCl]Cl with 2-phenylbenzthiazolidine (Ph-BtzH) and subsequent anion metathesis afforded the formamidinium salt [(Ph-Btz)CH(NiPr2)][PF6] ([1aH][PF6]). The reaction of [1aH][PF6] with (Me3Si)2NNa in the presence of grey selenium furnished the selenourea derivative 1aSe as trapping product of the acyclic diaminocarbene 1a. In the absence of selenium, a 2H-1,4-benzothiazine derivative (2) was obtained, which is an isomer of 1a, whose formation is plausibly initiated by deprotonation of [1aH]+ not at the cationic N2CH unit, but at the neighbouring PhCH position. CO was ineffective as trapping reagent for 1a. [1aH][PF6], 1aSe and 2 have been structurally characterised by X-ray diffraction.