Bulletin of the Chemical Society of Japan p. 1667 - 1672 (1996)
Update date:2022-08-25
Topics:
Taguchi, Yoichi
Tsuchiya, Tohru
Oishi, Akihiro
Shibuya, Isao
The [2 + 2]cycloaddition of phenyl isocyanate to 2,3-dihydrofuran was appreciably accelerated by compression to produce a β-lactam ring; its apparent activation volume was estimated to be -28 ml mol-1. Similar β-lactams were obtained under high pressure in the reaction of phenyl isocyanate with various vinyl ethers. Although the [2 + 2]cycloaddition of alkyl isocyanates to 2,3-dihydrofuran was also accelerated under high pressure to give β-lactams with good yields; the reactions of alkyl isocyanates with ethyl vinyl ether were slow, even at high pressure.
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