32730-85-1

Usage

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 5691, 1995 DOI: 10.1016/0040-4039(95)01125-2

InChI:InChI=1/C8H13N/c9-7-8-5-3-1-2-4-6-8/h8H,1-6H2

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 502-42-1 cycloheptanone 
• 18317-64-1 1-bromocycloheptene 
• 151-50-8 potassium cyanide 
• 88693-07-6 Cycloheptanone carbomethoxyhydrazone 
• 143-33-9 sodium cyanide 
• 124243-29-4 1-(1-Cyanocycloheptyl)-2-carbomethoxyhydrazine 
• 85688-89-7 1,1'-Bicycloheptyl-1,1'-dicarbonitril 
• 108-67-8 1,3,5-trimethyl-benzene 
• 1459-39-8 cycloheptanecarboxamide 
• 291-64-5 cycloheptane 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 502-41-0 cycloheptanol 
• 2453-46-5 cycloheptyl chloride 

Downstream Products

• 4448-77-5 cycloheptylmethylamine 
• 6004-52-0 cycloheptyl(phenyl)methanone 
• 1039766-42-1 C₁₄H₂₆N₂ 
• 1039765-88-2 C₁₉H₃₀N₂ 
• 1459-39-8 cycloheptanecarboxamide 

Relevant academic research and scientific papers

Thermodecarbonylation of α-substituted cycloalkanones: A convenient one-carbon ring contraction method

A new and very convenient one-carbon ring contraction method is reported. Pyrolysis of α-substituted cycloalkanones at 600-650°C under flow conditions produces the ring contracted compounds under loss of carbon monoxide. Substrates varying in ring size and nature of the α-substituent have been investigated.

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Dehydration of Amides to Nitriles under Conditions of a Catalytic Appel Reaction

A highly expedient protocol for a catalytic Appel-type dehydration of amides to nitriles has been developed that employs oxalyl chloride and triethylamine along with triphenylphosphine oxide as a catalyst. The reactions are usually complete in less than 10 min with only a 1 mol % catalyst loading. The reaction scope includes aromatic, heteroaromatic, and aliphatic amides, including derivatives of α-hydroxy and α-amino acids.

Photoinduced, Copper-Catalyzed Carbon-Carbon Bond Formation with Alkyl Electrophiles: Cyanation of Unactivated Secondary Alkyl Chlorides at Room Temperature

We have recently reported that, in the presence of light and a copper catalyst, nitrogen nucleophiles such as carbazoles and primary amides undergo C-N coupling with alkyl halides under mild conditions. In the present study, we establish that photoinduced, copper-catalyzed alkylation can also be applied to C-C bond formation, specifically, that the cyanation of unactivated secondary alkyl chlorides can be achieved at room temperature to afford nitriles, an important class of target molecules. Thus, in the presence of an inexpensive copper catalyst (CuI; no ligand coadditive) and a readily available light source (UVC compact fluorescent light bulb), a wide array of alkyl halides undergo cyanation in good yield. Our initial mechanistic studies are consistent with the hypothesis that an excited state of [Cu(CN)2]- may play a role, via single electron transfer, in this process. This investigation provides a rare example of a transition metal-catalyzed cyanation of an alkyl halide, as well as the first illustrations of photoinduced, copper-catalyzed alkylation with either a carbon nucleophile or a secondary alkyl chloride.

Generation of iminyl copper species from α-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere

Figure presented A copper-catalyzed reaction of α-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C-C bond cleavage of a transient iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from α-azidocarbonyl compounds and their C-C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O2 was found to be incorporated into the β-carbon fragment as a carboxylic acid.

Two-Carbon Elongation/Annulation of Alcohols to Nitriles

Alcohols were replaced by a two-carbon nitrile unit in good to excellent yields via dehydrative alkylation with (phenylsulfonyl)acetonitrile under modified Mitsunobu conditions followed by desulfonylation using magnesium.Diols and haloalcohols furnished cycloalkylnitriles.

Substituent Effects on the C-C-Bond Strength, 2. The Thermal Stability of Tetrasubstituted Succinonitriles

Rate constants and activation parameters for the thermolysis reaction of ten, partly cyclic tetraalkylsuccinonitriles and of meso-2,3-dimethyl-2,3-diphenylsuccinonitrile were determined.Relationships between ΔG* (300 deg C), ΔH* and ΔS* of the thermolysis reaction on the one hand and the change in strain enthalpy during bond dissociation on the other are pointed out.A force field procedure for the estimation of the strain in α-cyanoalkyl radicals is presented.A quantitative separation of the steric and resonance effects responsible for the thermal dissociation pro cess was achieved successfully.A resonance energy of 5.3 kcal*mol-1 was deduced for tertiary α-cyanoalkyl radicals in agreement with the most recent literature data.

Cyanation of 1-Halocycloalkenes Catalyzed by Tetracyanocobaltate(I). Convenient Synthesis of 1-Cyanocycloalkenes

1-Cyanocycloalkenes (1-cyanocyclopentene, -hexene, -heptene, and -octene) were readily synthesized by catalytic cyanation of the corresponding 1-halocycloalkenes with tetracyanocobaltate(I).Reactivities of methyl-substituted 1-chlorocyclohexenes were lower than that of 1-chlorocyclohexene, and 1-chloro-2-methylcyclohexene scarecely reacted.Hydrogenation and isomerization of 1-cyanocycloalkenes were observed only with 1-cyanocycloheptene and 1-cyano-6-methylcyclohexene, respectively.