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Showing metabocard for Acetic anhydride (HMDB0031646)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:37 UTC
Update Date2023-02-21 17:21:06 UTC
HMDB IDHMDB0031646
Secondary Accession Numbers
  • HMDB31646
Metabolite Identification
Common NameAcetic anhydride
DescriptionAcetic anhydride is an esterification agent for use in prepn. of modified food starch and for acetylation of monoglycerides Acetic anhydride is a versatile reagent for acetylations, the introduction of acetyl groups to organic substrates. In these conversions, acetic anhydride is viewed as a source of CH3CO+. Alcohols and amines are readily acetylated. For example, the reaction of acetic anhydride with ethanol yields ethyl acetate: (CH3CO)2O + CH3CH2OH → CH3CO2CH2CH3 + CH3COOH. Acetic anhydride is an irritant and flammable. Because of its reactivity toward water, alcohol foam or carbon dioxide are preferred for fire suppression. The vapour of acetic anhydride is harmful. Acetic anhydride is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with the moisture in the air. As indicated by its organic chemistry, Ac2O is mainly used for acetylations leading to commercially significant materials. Its largest application is for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. Similarly it is used in the production of aspirin, acetyl salicylic acid, which is prepared by the acetylation of salicylic acid. It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber. Because of its use for the synthesis of heroin by the diacetylation of morphine, acetic anhydride (known as 'AA' in clandestine chemistry circles) is listed as a U.S. DEA List II Precursor, and restricted in many other countries. The largest markets for diverted acetic anhydride continue to be heroin laboratories in Afghanistan
Structure
Data?1677000066
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031646 (Acetic anhydride)


  Mrv0541 05061306032D          

  7  6  0  0  0  0            999 V2000
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
Download

3D MOL for HMDB0031646 (Acetic anhydride)

HMDB0031646
     RDKit          3D
Acetic anhydride
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.5155    0.3765    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -0.3288    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2587   -1.5643    0.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    0.3267    0.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -0.3751    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2587    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1316   -1.5934    0.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289    0.0133   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884    1.4686    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446    0.2200    1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4529    1.3032   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -0.3694   -0.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9346    0.2640    1.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  6 11  1  0
  6 12  1  0
  6 13  1  0
M  END
Download

3D SDF for HMDB0031646 (Acetic anhydride)


  Mrv0541 05061306032D          

  7  6  0  0  0  0            999 V2000
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031646

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3

> <INCHI_KEY>
WFDIJRYMOXRFFG-UHFFFAOYSA-N

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.423829713825054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
acetyl acetate

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.3125194183333333

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.945086711302831

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
22.082000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetic anhydride

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0031646 (Acetic anhydride)

HMDB0031646
     RDKit          3D
Acetic anhydride
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.5155    0.3765    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -0.3288    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2587   -1.5643    0.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    0.3267    0.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1794   -0.3751    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2587    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1316   -1.5934    0.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289    0.0133   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884    1.4686    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446    0.2200    1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4529    1.3032   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -0.3694   -0.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9346    0.2640    1.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  6 11  1  0
  6 12  1  0
  6 13  1  0
M  END
Download

PDB for HMDB0031646 (Acetic anhydride)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5    7                                                  
CONECT    4    2    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0031646 (Acetic anhydride)

COMPND    HMDB0031646
HETATM    1  C1  UNL     1       2.515   0.376   0.130  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.219  -0.329   0.311  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.259  -1.564   0.580  1.00  0.00           O  
HETATM    4  O2  UNL     1      -0.013   0.327   0.193  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.179  -0.375   0.371  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.521   0.259   0.260  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.132  -1.593   0.636  1.00  0.00           O  
HETATM    8  H1  UNL     1       3.029   0.013  -0.781  1.00  0.00           H  
HETATM    9  H2  UNL     1       2.288   1.469   0.046  1.00  0.00           H  
HETATM   10  H3  UNL     1       3.145   0.220   1.034  1.00  0.00           H  
HETATM   11  H4  UNL     1      -2.453   1.303  -0.132  1.00  0.00           H  
HETATM   12  H5  UNL     1      -3.223  -0.369  -0.320  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.935   0.264   1.310  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   11   12   13
END
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SMILES for HMDB0031646 (Acetic anhydride)

CC(=O)OC(C)=O
Download

INCHI for HMDB0031646 (Acetic anhydride)

InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(CH3CO)2OChEBI
(MeCO)2OChEBI
Ac2OChEBI
AcetanhydrideChEBI
Acetic acid anhydrideChEBI
Acetyl acetateChEBI
Acetyl oxideChEBI
Anhydride acetiqueChEBI
EssigsaeureanhydridChEBI
Ethanoic anhydrateChEBI
Ethanoic anhydrideChEBI
Acetate anhydrideGenerator
Acetyl acetic acidGenerator
Ethanoic anhydric acidGenerator
Acetic acid, anhydrideHMDB
Acetic oxideHMDB
Acetyl anhydrideHMDB
Acetyl etherHMDB
Acetyltrimethyl-silaneHMDB
Anhydrid kyseliny octoveHMDB
Anidride aceticaHMDB
AzijnzuuranhydrideHMDB
Octowy bezwodnikHMDB
Acetic anhydride, 3H-labeledHMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Nameacetyl acetate
Traditional Nameacetic anhydride
CAS Registry Number108-24-7
SMILES
CC(=O)OC(C)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
InChI KeyWFDIJRYMOXRFFG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • Carboxylic acid anhydride
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-73 °CNot Available
Boiling Point137.00 to 140.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility120 mg/mL at 20 °CNot Available
LogP-0.480The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility119 g/LALOGPS
logP0.11ALOGPS
logP-0.31ChemAxon
logS0.07ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.08 m³·mol⁻¹ChemAxon
Polarizability9.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.0231661259
DarkChem[M-H]-113.82631661259
DeepCCS[M+H]+121.21130932474
DeepCCS[M-H]-119.31530932474
DeepCCS[M-2H]-155.00630932474
DeepCCS[M+Na]+129.44130932474
AllCCS[M+H]+125.832859911
AllCCS[M+H-H2O]+121.632859911
AllCCS[M+NH4]+129.832859911
AllCCS[M+Na]+131.032859911
AllCCS[M-H]-123.432859911
AllCCS[M+Na-2H]-127.332859911
AllCCS[M+HCOO]-131.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetic anhydrideCC(=O)OC(C)=O1223.5Standard polar33892256
Acetic anhydrideCC(=O)OC(C)=O629.8Standard non polar33892256
Acetic anhydrideCC(=O)OC(C)=O702.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetic anhydride GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-883c860e5905aab2532d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetic anhydride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetic anhydride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 10V, Positive-QTOFsplash10-0w29-9800000000-e55e60193ad8b633285a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 20V, Positive-QTOFsplash10-0w29-9800000000-5d2524434f33a1e79cc02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 40V, Positive-QTOFsplash10-0006-9000000000-8850b43805e8bf48f1f82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 10V, Negative-QTOFsplash10-0zfu-9600000000-2bf62658103ef9ea51372015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 20V, Negative-QTOFsplash10-0zfr-9600000000-0941637364d795b5d5dc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 40V, Negative-QTOFsplash10-052f-9000000000-6c6e84d48837a0409c372015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 10V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 40V, Negative-QTOFsplash10-0a4i-9000000000-8dc97f621de1cc9e2c112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 10V, Positive-QTOFsplash10-0006-9000000000-6aa1f4078505fa3b09712021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 20V, Positive-QTOFsplash10-0006-9000000000-87bbaed151efac0845912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetic anhydride 40V, Positive-QTOFsplash10-0006-9000000000-87bbaed151efac0845912021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008300
KNApSAcK IDNot Available
Chemspider ID7630
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetic_anhydride
METLIN IDNot Available
PubChem Compound7918
PDB IDNot Available
ChEBI ID36610
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1097401
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lou W, Zong M, Fan X, Lu J, Du W: [Asymmetric microbial reduction of organosilyl ketone with immobilized Saccharomyces cerevisiae cells]. Wei Sheng Wu Xue Bao. 2002 Aug;42(4):484-9. [PubMed:12557557 ]
  2. Pratap R, Ram VJ: An efficient de novo synthesis of partially reduced phenanthrenes through C-C insertion. J Org Chem. 2007 Sep 14;72(19):7402-5. Epub 2007 Aug 18. [PubMed:17705542 ]
  3. Li N, Zong MH, Liu C, Peng HS, Wu HC: (R)-oxynitrilase-catalysed synthesis of chiral silicon-containing aliphatic (R)-ketone-cyanohydrins. Biotechnol Lett. 2003 Feb;25(3):219-22. [PubMed:12882574 ]
  4. Huang SR, Liu SL, Zong MH, Xu R: Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal. Biotechnol Lett. 2005 Jan;27(2):79-82. [PubMed:15703868 ]
  5. Goel A, Verma D, Dixit M, Raghunandan R, Maulik PR: Acetyltrimethylsilane: a novel reagent for the transformation of 2H-pyran-2-ones to unsymmetrical biaryls. J Org Chem. 2006 Jan 20;71(2):804-7. [PubMed:16408998 ]
  6. Martin D, Illa O, Baceiredo A, Bertrand G, Ortuno RM, Branchadell V: Theoretical and experimental investigation of the basicity of phosphino(silyl)carbenes. J Org Chem. 2005 Jul 8;70(14):5671-7. [PubMed:15989352 ]
  7. Zhang BB, Cheng J, Lou WY, Wang P, Zong MH: Efficient anti-Prelog enantioselective reduction of acetyltrimethylsilane to (R)-1-trimethylsilylethanol by immobilized Candida parapsilosis CCTCC M203011 cells in ionic liquid-based biphasic systems. Microb Cell Fact. 2012 Aug 16;11:108. doi: 10.1186/1475-2859-11-108. [PubMed:22897972 ]
  8. Lefebvre O, Brigaud T, Portella C: Acetyltrimethylsilane, trifluoromethyltrimethylsilane, and prenyl esters: a three-component system for the synthesis of gem-difluoroanalogues of monoterpenes. J Org Chem. 2001 Jun 15;66(12):4348-51. [PubMed:11397175 ]
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