Science of Synthesis

Svatunek, D.; Houk, K. N., Science of Synthesis: Click Chemistry, (2021) 1, 429.

In 1971, Padwa et al. described the photocycloaddition of arylazirines with electron-deficient alkenes.[‌114‌] Upon irradiation, 3-phenyl-2H-azirine forms the corresponding nitrile ylide, which reacts readily and in high yields with dipolarophiles such as methyl acrylate to form pyrrolines ‌26‌ (‌Scheme 31‌). In 1976, a thorough experimental study into the photo and cycloaddition chemistry of such compounds was conducted,[‌115‌] and in 1999 cycloadditions of various 1,3-dipoles were investigated computationally.[‌116‌] These studies suggested that nitrile ylides are even more reactive than nitrile imines and also have to be produced in situ.

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References