Science of Synthesis

Wille, U., Science of Synthesis, (2009) 40, 911.

1-Chloroaziridines can be prepared from the corresponding aziridines in ca. 50% yield using readily available household bleach (ca. 0.8 M in sodium hypochlorite) (‌Scheme 32‌). Thus, when the aziridines ‌46‌ are reacted in this way the N-chlorinated products ‌47‌ are formed as mixtures of isomers. In the case of 1-chloro-2-methylaziridine (‌47‌, R1 = Me; R2 = R3 = H) the cis- and trans-isomers (with respect to the methyl and chlorine) have an interconversion barrier of about 110 kJ·mol−1 [‌160‌,‌173‌,‌174‌] and may be separated into the individual isomers by preparative gas chromatography.[‌175‌] The relative rates at which these products undergo solvolysis have been measured.[‌175‌,‌176‌] In related work, the C2-symmetric optically active 1-chloroaziridine ‌48‌ is prepared in an efficient manner from the parent aziridine by N-chlorination with aqueous sodium hypochlorite at 0°C (‌Scheme 32‌; see Section ‌40.4.2.1.3.3‌ for a comparable reaction with tert-butylhypochlorite).[‌177‌]

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References

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• 8.Meeeee-Meee, (8888) M 88e8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.