Aspects of the chemistry of 6-diazopenicillanate S-oxide and S,S-dioxide
Abstract
Procedures are developed for the preparation of 6-diazopenicillanate S-oxides and S,S-dioxides from the corresponding 6-phenylacetamidopenicillanates by N-nitrosation and thermal decomposition of the intermediate N-nitroso amides. The chemistry of these 6-diazopenicillanate S-oxides and S,S-dioxides was then briefly investigated, their reactions with pseudohalogens, alcohols, thiols, phenylseleno compounds, and aromatic aldehydes being examined. In some cases the products from these reactions were rearranged into the corresponding cepham or cephem derivatives.