Tosylmethyl isocyanide → 1,7,7-Trimethyl-bicyclo[2.2.1]heptane-2-carbonitrile

HRID 1018346Notes

Reaction equation

[C@:1]12([CH3:11])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=O.S([CH2:22][N+:23]#[C-])(C1C=CC(C)=CC=1)(=O)=O>>[CH3:11][C:1]12[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:2]2[C:22]#[N:23]

Participants

Reactant 2

HCID 161915Tosylmethyl isocyanide

HCID 9543187HCID 9543187, compound

Product 1

HCID 184055501,7,7-Trimethyl-bicyclo[2.2.1]heptane-2-carbonitrile

Procedure

(1R)-(+)-Camphor was converted to the nitrile using tosylmethyl isocyanide according to the procedure of O. H. Oldenziel (O. H. Oldenziel, D. van Leusen, and A. M. van Leusen J.Org.Chem. 1977, 42, 3114).

Sources & evidence

ORD record: ord-ab03afc53d47427c8a72abb2a6f741a2
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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