Anthracene → Anthracene isobutyl 2-cyanoacrylate

HRID 441537Notes

Reaction equation

[C:1]([C:3](=[CH2:11])[C:4]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5])#[N:2].C(OC(=O)C=C)#N.[CH:19]1[C:32]2[C:23](=[CH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=[CH:21][CH:20]=1>>[CH:22]1[C:23]2[C:32](=[CH:31][C:30]3[C:25]([CH:24]=2)=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:19]=[CH:20][CH:21]=1.[C:1]([C:3](=[CH2:11])[C:4]([O:6][CH2:7][CH:8]([CH3:9])[CH3:10])=[O:5])#[N:2]

Participants

Reactant 3

HCID 8418Anthracene

HCID 14046Isobutyl 2-cyanoacrylate

HCID 9942124Acrylcyanate

Product 1

HCID 21419273Anthracene isobutyl 2-cyanoacrylate

Procedure

The preferred dieneophile is isobutyl 2-cyanoacrylate, and the reaction of this latter cyanoacrylate with anthracene will yield the anthracene/isobutyl 2-cyanoacrylate adduct (II) in nearly quantitative yield.

Sources & evidence

ORD record: ord-76fd9252b4fe44b2b41ff3936a5c1997
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04041062

Reaction notes

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