Ethyl nitrodiazoacetate

Other alkenes can be cyclopropanated with nitrodiazo compounds in the same manner. Table 1 presents a survey. In the case of cycloadducts with ethyl nitrodiazoacetate, it is even possible to separate the diastereomeric cyclopropanes by partial saponification of the less sterically hindered isomer. ... 

Approximately 0.13 mol of crude ethyl nitrodiazoacetate (prepared as described in reference 2) is diluted with 10 mL of CH,C12 and added dropwise over 1 h, from a jacketed addilion funnel cooled with icc water, to a mixture of 15 g (0.13 mol) of phenylethene and 100 mg (0.25 mmol) of rhodium(II) acetate in 5 mL of CHjCL at 5 °C. When nitrogen evolution ceases (2 h), the mixture is stirred for an additional hour and then concentrated and filtered through flash silica gel. Elution with pentane removes excess phenylethene and then elution with hexane, Ht,0 4 1 provides the product as an oil yield 21.0 g (85%) d.r. (cisjtram ) 11 89. 

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See also in sourсe #XX -- [ ]

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