Transformation of β-Nitro Alcohols to the Corresponding Nitro Imines with Lithium Hexamethyldisilazide (LHMDS) via Sequential Retro Nitro-Aldol–Nitro-Mannich Reaction

Seiji Tanaka Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Chiba, JapanCorrespondence[email protected]

Kazuhiro Kochi Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Chiba, Japan

Hiroyuki Ito Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Chiba, Japan

Jun Mukawa Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Chiba, Japan

Keiki Kishikawa Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Chiba, Japan

Makoto Yamamoto Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Chiba, Japan

Shigeo Kohmoto Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, Chiba, Japan

show all

Abstract

β-Nitro alcohols were converted to the corresponding nitro imines in the presence of lithium hexmethyldisilazide (LHMDS) in one pot. The formal transformation of the hydroxy to imino group proceeded in a sequence of the retro nitro-aldol reaction of β-nitro alcohols and the double nitro-Mannich reaction of the resulting aldimines and nitro alkane dianions.

Keywords:

Notes

^a β-Nitro alcohols were added to the solution of LHMDS at the temperature mentioned.

^bNo reaction.

^cThe ratios were determined by ¹H NMR spectroscopy.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Transformation of β-Nitro Alcohols to the Corresponding Nitro Imines with Lithium Hexamethyldisilazide (LHMDS) via Sequential Retro Nitro-Aldol–Nitro-Mannich Reaction

Information for

Open access

Opportunities

Help and information

Transformation of β-Nitro Alcohols to the Corresponding Nitro Imines with Lithium Hexamethyldisilazide (LHMDS) via Sequential Retro Nitro-Aldol–Nitro-Mannich Reaction

Abstract

Notes

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature