1961
DOI: 10.1021/jo01062a031
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Studies on l-Alkenyl Isocyanates and Their Derivatives1

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Cited by 40 publications
(23 citation statements)
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“…For a number of reasons, our selected transformation is an ideal probe of the efficacy of the photothermal effect for driving bond formation. First, the formation of urethane is spontaneous at room temperature, 1 , 3 , 5 , 7 , 23 , 24 and this provides a baseline rate of bond formation to which we can compare the effect of photothermal heating. Second, there are many known chemical catalysts for this reaction – the most common being dibutyltin dilaurate (DBTDL) 25 , 26 – to which we can also compare the efficacy of the photothermal effect.…”
Section: Resultsmentioning
confidence: 99%
“…For a number of reasons, our selected transformation is an ideal probe of the efficacy of the photothermal effect for driving bond formation. First, the formation of urethane is spontaneous at room temperature, 1 , 3 , 5 , 7 , 23 , 24 and this provides a baseline rate of bond formation to which we can compare the effect of photothermal heating. Second, there are many known chemical catalysts for this reaction – the most common being dibutyltin dilaurate (DBTDL) 25 , 26 – to which we can also compare the efficacy of the photothermal effect.…”
Section: Resultsmentioning
confidence: 99%
“…The isomerization of N -allylamides, 14 oxidative amidation of alkenes, 15 and co-dimerization of N -vinyl amides with alkenes 16 all furnish the thermodynamically favorable E -isomer as the major product. Only few synthetic methods, such as the Curtius rearrangement of α,β-unsaturated acyl azides, 17 Peterson elimination, 18 transition metal-catalyzed cross-coupling reactions of vinyl halides, 19 vinyl triflates, 20 or vinyl ethers, 21 are applicable for the synthesis of the thermodynamically less favorable Z -isomer, but here, the starting materials are poorly available and expensive.…”
Section: Introductionmentioning
confidence: 99%
“…Methylvinyl isocyanate (3) was prepared via Curtius reaction from methacryloyl acyl chloride and sodium azide 17,[22][23][24] . The crude product was purified by fractionated distillation under a nitrogen atmosphere and stored at -18 8C.…”
Section: Monomer Synthesismentioning
confidence: 99%