PubMed · 10107215
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C Tokarski. 1990-10-15. Study strips Agent Orange link.. https://pubmed.ncbi.nlm.nih.gov/10107215/
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6-Bromomethyl-4H-1,3-dioxin has been prepared in three steps from allyl iodide. A variety of enolates were then alkylated with this bromide. The resulting 6-alkyl-4H-1,3-dioxins were either subjected to further multistep transformations and/or heated to effect facile retrocycloaddition reactions. The resulting enones smoothly participated in novel endo-conjugate addition reactions with both carbon and nitrogen nucleophiles. For example, several bicyclo[4.3.1]decan-3,10-diones, the carbon framework of the CP compounds, were constructed using this novel annulation strategy. In another natural product study, a benzazocine related to the heterocyclic framework of the ring-opened tautomeric form of FR-900482 was also prepared using this methodology. Finally, a piperidin-4-one obtained from a 6-endo conjugate addition was converted to the naturally occurring (2S,4R)-4-hydroxypipecolic acid. Collectively, these examples document the synthetic equivalency of dioxin 1 with bromomethyl vinyl ketone and, moreover, delineate a strategy for accomplishing the sequential reactions with nucleophiles at the alpha' followed by the beta electrophilic sites.
A novel Life-Cycle Assessment model (Fire-LCA) has been defined for the determination of the environmental impact of measures taken to attain a high level of fire safety. This study, which represents the first application of this LCA model, concentrates on a comparison between a TV with an enclosure manufactured with a flame retardant (FR) plastic (V0-rated high impact polystyrene, HIPS, typical for the US market) and one manufactured with a non-flame retardant (HB-rated HIPS, typical for the European market). A fire model has been defined based on international statistics, which indicate that use of V0 rated enclosure material essentially removes the risk of TV fires while approximately 165 TV fires occur per million TVs in Europe each year where the enclosure material is breached. The application of the model indicates that emissions of some key species (such as dibenzodioxins and PAH) are actually lower for the TV with the FR enclosure than for the TV with the NFR enclosure. This has direct reprercussions for the assessment of the environmental impact of the FR TV relative to that of the NFR TV. Finally, when considering the risk associated with the use of flame retardants, it is also important to consider the risk associated with fires. Based on the in-depth analysis of available fire statistics, conducted as a part of this study, it has been estimated that as many as 160 people may die each year in Europe as a direct result of TV fires and as many as 2000 may be injured in the same period.