Journal of the Chemical Society. Perkin transactions I p. 413 - 417 (1984)
Update date:2022-08-04
Topics:
Balsamo, Aldo
Benedini, Paola Maria
Macchia, Bruno
Macchia, Franco
Rossello, Armando
The azetidinone disulphide (1b), a structural analogue of Kamiya's disulphide (1a), has been synthesized.Some cyclization reactions of the disulphides (1) (Br2 in CH2Cl2 and AcOAg in ClCH2CO2H-CH2Cl2) leading to penal and cepham derivatives through episulphonium ions (2), have been studies.The data obtained show that changing the substituent X in (1a) and (1b) brings about changes in the distribution of the positive charge in the intermediate episulphonium ions (2a) and (2b), and thus affects to some extent the regioselectivity of the episulphonium ring opening and the chemical behaviour of (1a) and (1b).
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