PubMed · 10543156
The source did not provide an abstract. Follow the original record for more information.
Explore connections, maps & timelines
H Matsuki, Y Kawano. 1999. [Dioxin].. https://pubmed.ncbi.nlm.nih.gov/10543156/
Cite the original work for its findings. Save a collection to share your selection of sources.
KEEP EXPLORING
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.
The Emission Measurement Center (EMC) in the Environmental Protection Agency's Office of Air Quality Planning and Standards was directed to conduct an emissions test program at a sewage sludge incinerator in support of a Maximum Achievable Control Technology (MACT) standard. One pollutant category of concern at these facilities was polychlorinated biphenyls, or PCBs. An objective of the test program was to measure co-planar PCBs in the incinerator emissions, the sewage sludge introduced to the incinerator, and the scrubber water effluent used in controlling the incinerator emissions. Co-planar PCB congeners are those having four or more chlorine atoms with only a few substitutions in the ortho positions, i.e. positions designated 2, 2', 6, and 6'. Thirteen PCB compounds are sometimes referred to as the "WHO PCBs," because the World Health Organization (WHO) has derived toxic equivalency factors for these congeners. Studies have shown that these dioxin-like compounds can react with the aryl hydrocarbon receptor. This same reaction is believed to initiate adverse health effects for dioxin and furan congeners. In order to conduct the co-planer PCB testing, the EMC had to develop analytical methods that could measure the 13 co-planar PCBs. The purpose of the test program was to develop, evaluate, and implement analytical test methods capable of measuring co-planar PCBs in three matrices: incinerator stack gases, sewage sludge, and scrubber water effluents. The paper summarizes the initial development work that was performed in preparation of analytical test protocols that could measure co-planar PCBs in air, water, and sludge matrices. Following the method development, a MACT emissions test program was conducted at a sewage sludge facility in July 1999 and these data are also summarized in the paper.