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C3H4O

From Wikipedia, the free encyclopedia

C3H4O is a chemical formula that represents each of several actual and hypothetical compounds that differ in structure, but each consist of three atoms of carbon, four of hydrogen, and one of oxygen. The following compounds are among them:

Name CAS # Notes Structure
Oxetene, 2H-Oxete 287-25-2 Synthesized;[1] unstable.[2] Can be made by using light to cyclize acrolein.[3]
2-Oxabicyclo[1.1.0]butane[4] 35553-05-0
Acrolein, 2-propenal 107-02-8 Forms from pollutants, burning, metabolism.[5] Cis and trans forms; cis form predominant.[5]
Propa-1,2-dien-1-ol[6] 81788-96-7 Synthesized.[7] Tautomerizes "quantitatively" to acrolein above -50° C.[7]
Propargyl alcohol or 2-propyn-1-ol 107-19-7 "Mild, geranium odor"[8] Used in synthesis, as corrosion inhibitor, soil fumigant.[9]
Methoxy ethyne, methoxyacetylene 6443-91-0
Prop-1-yn-1-ol,[10] 1-propynol[11] 6175-54-8
Methylketene or 1-propen-1-one[12] 6004-44-0 Synthesized.[13] Intermediate in acrolein pyrolysis.[14] Of astronomical interest.[13]
Methylene oxirane,[15] allene oxide 40079-14-9 Synthesized;[16] predicted (1968) to isomerize "readily" to cyclopropanone.[16][17][needs update]
Cyclopropanone 5009-27-8 Synthesized; unstable due to polymerization and ring-opening.[18] Derivatives used in synthesis, biology.[18]

Tautomer of 1-cyclopen-1-ol[citation needed]

Cycloprop-1-en-1-ol, cyclopropene alcohol[19] 81788-95-6 Tautomer of cyclopropanone; Not synthesized[citation needed]
2-Cyclopropenol or 1-hydroxy-2-cyclopropene[dubious – discuss] 81788-94-5 Not synthesized[citation needed]
1,2-Epoxypropene or 2-methyloxirene[20] 2835-41-8 Synthesized; unstable. Product of ionized diazoacetone; isomerizes "rapidly" to methylketene, acrolein, methoxyethyne, and/or 1-propynol.[21][22]

References

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  1. ^ Friedrich, Louis E.; Lam, Patrick Yuk-Sun (1981-01-01). "Syntheses and reactions of 3-phenyloxete and the parent unsubstituted oxete". The Journal of Organic Chemistry. 46 (2): 306–311. doi:10.1021/jo00315a016. ISSN 0022-3263.
  2. ^ Ji Ram, Vishnu; Sethi, Arun; Nath, Mahendra; Pratap, Ramendra (2019-01-01), Ji Ram, Vishnu; Sethi, Arun; Nath, Mahendra; Pratap, Ramendra (eds.), "Chapter 4 - Four-Membered Heterocycles", The Chemistry of Heterocycles, Elsevier, pp. 93–147, ISBN 978-0-08-101033-4, retrieved 2024-12-08
  3. ^ Kikuchi O. (1981). "A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems". Tetrahedron Lett. 22 (9): 859–862. doi:10.1016/0040-4039(81)80015-9.
  4. ^ "2-Oxabicyclo[1.1.0]butane". PubChem. National Center for Biotechnology Information.
  5. ^ a b Puzzarini, Cristina; Penocchio, Emanuele; Biczysko, Malgorzata; Barone, Vincenzo (2014-08-21). "Molecular Structure and Spectroscopic Signatures of Acrolein: Theory Meets Experiment". The Journal of Physical Chemistry A. 118 (33): 6648–6656. Bibcode:2014JPCA..118.6648P. doi:10.1021/jp503672g. ISSN 1089-5639. PMID 24842714.
  6. ^ "Propa-1,2-dien-1-ol". PubChem. National Center for Biotechnology Information.
  7. ^ a b Hakiki, Abdelhak; Ripoll, Jean-Louis; Thuillier, André (1984-01-01). "Retrodienic reactions XVI - flash thermolytic generation of reactive functional allenes". Tetrahedron Letters. 25 (32): 3459–3460. doi:10.1016/S0040-4039(01)91046-9. ISSN 0040-4039.
  8. ^ "Propargyl alcohol". NIOSH Pocket Guide to Safety and Hazards. National Institute for Occupational Safety and Health. Retrieved 2024-12-08.
  9. ^ "Propargyl alcohol". PubChem. National Center for Biotechnology Information.
  10. ^ "CID 141504292". PubChem. National Center for Biotechnology Information.
  11. ^ "NIST Chemistry WebBook, SRD 69: 1-Propynol". NIST. Retrieved 8 December 2024.
  12. ^ "Methylketene". PubChem. National Center for Biotechnology Information.
  13. ^ a b Derbali, Imene; Hrodmarsson, Helgi Rafn; Schwell, Martin; Bénilan, Yves; Poisson, Lionel; Hochlaf, Majdi; Alikhani, Mohammad Esmaïl; Guillemin, Jean-Claude; Zins, Emilie-Laure (2020-09-23). "Unimolecular decomposition of methyl ketene and its dimer in the gas phase: theory and experiment". Physical Chemistry Chemical Physics. 22 (36): 20394–20408. Bibcode:2020PCCP...2220394D. doi:10.1039/D0CP03921G. ISSN 1463-9084.
  14. ^ Muzika, Michael; Genossar-Dan, Nadav; Fux, Dana; Har Lavan, Shani; Zamir, Uri; Rozenberg, Illya; Hemberger, Patrick; Baraban, Joshua H. (2024-04-01). "Radical intermediates and stable products in acrolein pyrolysis". Environmental Chemistry Letters. 22 (2): 491–497. doi:10.1007/s10311-023-01661-8. ISSN 1610-3661.
  15. ^ "Methyleneoxirane". PubChem. National Center for Biotechnology Information.
  16. ^ a b Turecek, Frantisek; Drinkwater, Donald E.; McLafferty, Fred W. (1990-07-01). "The elusive methyleneoxirane: preparation and characterization by flash-vacuum pyrolysis and neutralization-reionization mass spectrometry". Journal of the American Chemical Society. 112 (15): 5892–5893. Bibcode:1990JAChS.112.5892T. doi:10.1021/ja00171a046. ISSN 0002-7863.
  17. ^ Hoffmann, Roald (March 1968). "Trimethylene and the addition of methylene to ethylene". Journal of the American Chemical Society. 90 (6): 1475–1485. Bibcode:1968JAChS..90.1475H. doi:10.1021/ja01008a016. ISSN 0002-7863.
  18. ^ a b Wasserman, Harry H.; Berdahl, Donald R.; Lu, Ta-Jung (1987-10-28), Rappoport, Zvi (ed.), "The Chemistry of Cyclopropanones", Cyclopropyl Group Volume 1 and Volume 2 (1987), Chichester, UK: John Wiley & Sons, Ltd, pp. 1455–1532, doi:10.1002/0470023449.ch23, ISBN 978-0-470-02344-0, retrieved 2024-12-08
  19. ^ "Cycloprop-1-en-1-ol". PubChem. National Center for Biotechnology Information.
  20. ^ "2-Methyloxirene". PubChem. National Center for Biotechnology Information.
  21. ^ Lewars, Errol G. (2008), Lewars, Errol G. (ed.), "Oxirene", Modeling Marvels: Computational Anticipation of Novel Molecules, Dordrecht: Springer Netherlands, pp. 31–52, doi:10.1007/978-1-4020-6973-4_3, ISBN 978-1-4020-6973-4, retrieved 2024-12-08
  22. ^ Turecek, Frantisek; Drinkwater, Donald E.; McLafferty, Fred W. (1991-07-01). "Gas-phase formation and rearrangements of methyloxirene and its cation radical". Journal of the American Chemical Society. 113 (16): 5958–5964. Bibcode:1991JAChS.113.5958T. doi:10.1021/ja00016a006. ISSN 0002-7863.


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