The unusual electronic properties and unique reactivity of fulvenes have interested researchers for over a century. The propensity to form dipolar structures at relatively low temperatures and to participate as various components in cycloaddition reactions, often highly selectively, makes them ideal for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes. Tables providing comprehensive directories of fulvene cycloaddition chemistry are provided, including fulvene intramolecular and intermolecular cycloadditions complete with reactant partners and their resulting cyclic adducts, which provide a useful reference source for synthetic chemists working with fulvenes and complex polycyclic scaffolds.
1,1-Dichloro-2,2,2-trifluoroethane (HCFC-123) was evaluated as a substitute for trichlorofluoromethane (CFC-11), and it appeared that a permissible exposure limit of 50 ppm was justified. When HCFC-123 was introduced as a precision cleaning agent in a controlled operation, marked elevations in serum alanine transaminase and serum aspartase transaminase were noted in exposed workers. Sampling taken during start-up documented personal samples from 24-480 ppm (375 and 21 min, respectively) and area samples of 18-180 ppm (375 and 21 min, respectively). Personal and area samples collected after the liver abnormalities were identified ranged from 5-12 ppm. Exposure data were not available for the period when the abnormalities are suspected to have developed. Two models were developed to estimate exposure during the unmonitored period: (1) the entire plant as a homogenous box and (2) evaporation into smaller work zones. Modeling using the entire building estimated 8-hour time-weighted average (TWA) exposures of 10-35 ppm. Modeled estimates of work area and air exchange rates indicated that degreaser exposed workers could have experienced peak levels of 280-2,100 ppm (8-hour TWAs 252-1,630 ppm). Modeling of the work environment, estimated to be one-third of the volume of the entire open building, indicated peak exposures of 28-210 ppm (8-hour TWAs 25-163 ppm). These ranges estimate the minimum and maximum exposure levels. The best estimates, using 12 air changes per day, suggest peak levels around the degreaser of 635-2,100 ppm (8-hour TWA 499-1,630 ppm) and 63-207 ppm (8-hour TWAs 50-163 ppm) in the work area. These are the first estimates of exposure level associated with these hepatotoxic effects; all are significantly higher than personal and area samples collected for HCFC-123 after the liver abnormalities were identified.
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