Darstellung von aliphatischen Immoniumverbindungen mit Orthoameisensäureester als wasserbindendes Mittel

Nikolajewski, H. E.; Däuhne, Siegfried; Hirsch, B.

doi:10.1002/zfch.19680080209

Zeitschrift fuer Chemie

1968

DOI: 10.1002/zfch.19680080209

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Darstellung von aliphatischen Immoniumverbindungen mit Orthoameisensäureester als wasserbindendes Mittel

H. E. Nikolajewski¹,

Siegfried Däuhne²,

B. Hirsch³

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1977

1979

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The reductive animation of 4‐tert‐butylcyclohexanone with an NADH model

Nie-Sarink

Pandit

1979

Recl. Trav. Chim. Pays‐Bas

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4-tert-Butylcyclohexanone undergoes reductive amination to a mixture of isomeric 1 -pyrrolidino-4-tert-butylcyclohexanes (3a,b) upon reduction with Hantzsch ester (2), in the presence of pyrrolidine and the corresponding perchlorate. Under standardized conditions (10 equiv. of pyrrolidine, 1 equiv. of pyrrolidine perchlorate), only 75 % of the product (3a,b) is formed via XduG tion by the Hantzsch ester. The remaining 25% is produced in a process which involves a hydride transfer from either the pyrrolidine (secondary amine) or the enamine system, generated as an intermediate in the reaction to the corresponding iminium salt. The stereochemistry of the Hantzsch ester reduction has been investigated by the use of 4,4-dideutero-Hantzsch ester (7).

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The reductive animation of 4‐tert‐butylcyclohexanone with an NADH model

Nie-Sarink

Pandit

1979

Recl. Trav. Chim. Pays‐Bas

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Vorsicht beim Umgang mit Perchloraten organischer Basen!

Menzer¹,

Kazmirowski²

1977

Zeitschrift fuer Chemie

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Darstellung von aliphatischen Immoniumverbindungen mit Orthoameisensäureester als wasserbindendes Mittel

Cited by 2 publications

References 1 publication

The reductive animation of 4‐tert‐butylcyclohexanone with an NADH model

The reductive animation of 4‐tert‐butylcyclohexanone with an NADH model

Vorsicht beim Umgang mit Perchloraten organischer Basen!

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