Synthesis of α-(trifluoromethyl)phenylacetonitrile. Anomalous reactions of α-tosyloxy-α-(trifluoromethyl)phenylacetonitrile with sodium borohydride

Németh, Gábor; Poszácz, László; Bozsing, D.; Simig, Gyula

doi:10.1016/0022-1139(96)03433-1

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The Radical Pathway1

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Cited by 7 publications

(5 citation statements)

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“…The reductive decyanation promoted by aluminium- and borohydrides for substrates other than α-aminonitriles has been described for more specific cases and usually displays moderate yields [ 76 – 79 ]. Recently, the DIBAL-H-induced decyanation of gem -dicyanodihydroazulene derivatives was described but only poor yields were reported [ 80 ].…”

Section: Reviewmentioning

confidence: 99%

The reductive decyanation reaction: an overview and recent developments

Mattalia¹

2017

Beilstein J. Org. Chem.

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Section: Reviewmentioning

confidence: 99%

The reductive decyanation reaction: an overview and recent developments

Mattalia¹

2017

Beilstein J. Org. Chem.

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“…An anomalous reduction of α-tosyloxy-α-(trifluoromethyl)phenylacetonitrile 36 with NaBH 4 in DMSO was described by Németh et al 96 Since S N was disfavored by steric (S N 2) and electronic (S N 1) factors, the authors proposed a single electron-transfer (SET) process (Scheme 16).…”

Section: Scheme 15mentioning

confidence: 99%

The reductive decyanation reaction: chemical methods and synthetic applications

Mattalia¹,

Marchi-Delapierre²,

Hazimeh³

et al. 2006

Arkivoc

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Several sequences involving the nitrile group require the removal of this function in a convenient and clean procedure. This transformation, called reductive decyanation, has received much attention over the years. In this review, we describe the chemical methods leading to reductive decyanation as well as the proposed mechanisms. Much of these methodologies proceed with good yields and stereoselectivities allowing their exploitation in organic synthesis.

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“…28 Eberson estimated the standard potential of AlH 4 Á /AlH 4 À redox couple as E°o x = À(0.1-0.3 V) vs NHE in THF. 29 House discussed possible electron transfer between carbanions and unsaturated carbonyl compounds in terms of the difference in standard electrode potentials.…”

Section: The Radical Pathwaymentioning

confidence: 99%