The anaerobic biodegradation of surfactants is used as an acceptability criterion in some environmental pieces of legislation (eco-label, risk assessment, etc.), without a proper evaluation of the relevance of such a characteristic. Available screening test methods to assess the anaerobic biodegradation do not simulate the real conditions prevailing in these anaerobic compartments but rather reflect more stringent conditions, due to the high test substance/biomass ratio, possibility of inhibitory effects and limited possibility for adaptation. Therefore positive results are indicative of a similar behaviour under environmental conditions, while a negative result cannot be necessarily interpreted as inherent anaerobic recalcitrance. The majority of surfactants entering the environment will be exposed to and degraded under aerobic conditions, and only less than 20 % will potentially reach temporarily anaerobic environmental compartments. In contrast to the well documented adverse effects observed in the absence of aerobic biodegradation, the lack of anaerobic biodegradation does not seem to be correlated with any apparent environmental problem for most compartments after more than 40 years of widely use of such products. The scientific review concluded that anaerobic biodegradability does not have the same environmental relevance as the aerobic one. Anaerobic biodegradability should not, therefore, be used as a pass/fail property for the environmental acceptability of surfactants which are readily biodegradable under aerobic conditions.

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2-Aminothioisomünchnones, a well-known family of masked dipoles, react with aromatic aldehydes in a domino cascade reaction that produces episulfides (thiiranes) or beta-lactams (2-azetidinones). This sequence is initiated by a [3+2] dipolar cycloaddition followed by ring opening of cycloadducts and intramolecular rearrangement to afford these unusual ring contractions. The nature of the reaction products depends on the structural characteristics of the starting dipole and the experimental conditions. Episulfides are obtained selectively as cis isomers with respect to both aryl groups, whereas beta-lactams are produced as cis/trans mixtures. These structural features were determined unequivocally by X-ray crystallographic analysis. The beta-lactams still possessed a flexible acyclic chain containing sulfur, a salient lead modification of the bioactive cyclic penems and cephems. The preferential production of exo transition structures was rationalized with the aid of computational calculations at the B3LYP/6-31G* level.

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