Liquid-phase noncatalytic oxidation of monoterpenoids with nitrous oxide

Romanenko, E. P.; Starokon, E. V.; Panov, G. I.; Tkacheva, Anastasia

doi:10.1007/s11172-007-0187-9

Cited by 5 publications

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References 9 publications

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“…Oxidation of 2 with N 2 O in benzene was reported to proceed with low levels of conversion (19 %) but high selectivity for 1 (83 %) accompanied by myrtanal (6 %) 26. Reactions were carried out in stainless steel autoclaves at 250 °C and an autogenous pressure of 5–7 MPa (initial = 2.5 MPa).…”

Section: Synthesis From β‐Pinene With Other Oxidantsmentioning

confidence: 99%

Synthesis of Nopinone from β‐Pinene – A Journey Revisiting Methods for Oxidative Cleavage of C=C Bonds in Terpenoid Chemistry

Stolle

2013

Eur J Org Chem

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The easily accessible 2‐(methylamino)pyridinato titanium complex initially synthesized by Kempe is used as catalyst for efficient intramolecular hydroaminoalkylation reactions of secondary aminoalkenes. The corresponding reactions of N‐aryl‐substituted 1‐aminohept‐6‐enes and 1‐aminohex‐5‐enes directly give access to 2‐methylcyclohexyl‐ or 2‐methylcyclopentylamines in good yields. In addition, intramolecular hydroaminoalkylations of an N‐alkyl‐substituted secondary aminoalkene and a geminally β‐disubstituted substrate are described for the first time. While all products are formed as mixtures of two diastereoisomers, better trans/cis ratios are observed during the formation of 2‐methylcylopentylamines.

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Section: Synthesis From β‐Pinene With Other Oxidantsmentioning

confidence: 99%