- mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives
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A mCPBA-mediated, metal-free, intramolecular dioxygenation reaction of unactivated alkenes is reported. In the presence of m-chlorobenzoic peracid, different unsaturated amide substrates could be cyclized via epoxide intermediates, producing the corresponding 5-imino-2-tetrahydrofuranyl methanol products in up to 94% yield at room temperature.
- Deng, Xiaojun,Zhang, Luwen,Liu, Huixia,Bai, Yu,He, Wei
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supporting information
(2020/11/24)
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- Deamination Reactions, 46. - Decomposition of 1-Alkenylcyclopropanediazonium Ions
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1-(2-Propenyl)- (10a), 1-(2-methyl-2-propenyl)- (10b), and 1-(3-butenyl)cyclopropanediazonium ions (35) have been generated by alkaline cleavage of the analogous nitrosocarbamates in methanol.Their major reaction paths are cyclopropyl-allyl tranformation (67 - 81percent), elimination to give alkylidenecyclopropanes (13 - 21percent), nucleophilic displacement (4 - 6percent), and 1,2-H shift (1 - 5percent).Participation of the double bond with formation of spirocyclic products was found to be small (0.5 - 1.2percent) with 10a, b and negligible with 35.The 2-methylene-5-hexenyl cations (39) arising from 35 underwent cyclization (intramolecular electrophilic addition, 39 --> 42) in competition with nucleophilic capture, but did not undergo a degenerate Cope rearrangement (39 39').
- Kirmse, Wolfgang,Rode, Klaus
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p. 839 - 846
(2007/10/02)
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