One of the main objectives in current chemical process development is increasing laboratory efficiency by high throughput experimentation (HTE) for screening of reaction and process parameters and by high speed experimentation (HSE) for optimisation of process parameters. An important tool in reaching this second goal is the use of parallel automated reactor systems. This report describes the tests, requirements, and evaluation scheme we used in our laboratories for testing three commercially available systems.
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The dianion of acenaphthylene can be converted into the 5‐hydroanion by protonation with one equivalent of methanol. Subsequent reaction with electrophiles such as allyl bromide and propargyl bromide occurs selectively at position 1, resulting in the formation of the novel 1‐allylacenaphthene and 1‐propargylacenaphthene. In addition to what was observed in the case of methyl iodide, the hitherto unknown 1,1‐dialkylated acenaphthene derivatives are formed as minor products; probably the lower reactivity of the unsaturated bromides is responsible for this side reaction. From the products of the reactions with 3,3‐dimethylallyl bromide and (bromomethyl)cyclopropane the mechanism was found to be SN2. Reaction of the hydroanion with benzyl bromide takes place at position 1 as well as at position 2a. The reactivity of carbon 2a towards the soft electrophile benzyl bromide is attributed to the high HOMO coefficient at this position.
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