Organic Reactions in Water: Highly Rapid CAN Mediated One-Pot Synthesis of Nitriles from Aldehydes under Mild Conditions

B. P.  Bandgar; S. S.  Makone

doi:10.1055/s-2003-36779

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Synlett 2003(2): 0262-0264
DOI: 10.1055/s-2003-36779

LETTER

Organic Reactions in Water: Highly Rapid CAN Mediated One-Pot Synthesis of Nitriles from Aldehydes under Mild Conditions

B. P. Bandgar*, S. S. Makone
Organic Chemistry Research Laboratory, School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Vishnupuri, Nanded-431 606, India
Fax: +91(2462)29245; e-Mail: bandgar_bp@yahoo.com;

Further Information

Publication History

Received 2 December 2002
Publication Date:
22 January 2003 (online)

Abstract
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Abstract

A variety of aliphatic and aromatic nitriles were prepared from the corresponding aldehydes in high yield in a direct one pot and rapid process using ceric ammonium nitrate (CAN) in amonia-water under mild conditions.

Key words

ceric ammonium nitrate (CAN) - aldehydes - nitriles - organic reactions in water

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14

(14)(3,4,5-Triacetoxy)pentanenitrile (15): [α]_D ²⁵ 7.3 (c 2.6, CHCl₃). IR (neat): 2265cm^-1. ¹H NMR (300 MHz, CDCl₃): δ = 2.1 (s, 3 H, COCH₃), 2.15 (s, 3 H, COCH₃), 2.18 (s, 3 H, COCH₃), 2.6-2.7 (m, 2 H, CH₂CN), 4.15 (dd, J = 12.2 and 4.5 Hz, 1 H), 4.35 (dd, J = 12.2 and 3.3 Hz, 1 H), 5.2-5.3 (m, 2 H, CH₂O). ¹³C NMR (75 MHz, CDCl₃): δ = 17 (CH₂), 21 (2 × CH₃), 22.5 (CH₃), 62.3(CH₂), 65.7 (CH), 72.1 (CH), 123.2 (C), 171.4 (C), 171.8 (C), 172.1 (C). Anal. Calcd for C₁₁H₁₅O₆N (257.24): C, 51.36; H, 5.88; N, 5, 45. Found: C, 51.41; H, 5.71; N, 5.49.