Journal of Organic Chemistry p. 1688 - 1691 (1984)
Update date:2022-08-04
Topics:
Snider, Barry B.
Cartaya-Marin, Claudia P.
(+/-)-Nitramine (1a) was synthesized in seven steps from methylenecyclohexane in 33percent overall yield.A three-step sequence was developed from methylenecyclohexane to aldehyde 4 in which methyl α-chloroacrylate was used as a ketene equivalent in the ene reaction.Aldehyde 4 was converted to nitrone 3 which cyclized to a 2.5:1 mixture of 2 and 9.Hydrogenolysis of 2 gave 1a.Lewis acid catalyzed cyclization of 4 gave a 3.5:1 mixture of hydrindanones 13 and 14 at 25 deg C and a 12:1 mixture of 13 and 14 at -20 deg C.
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