Cyclobutène

cyclobutène
Identification
Nom UICPA cyclobutène
No CAS 822-35-5
No ECHA 100.011.360
No CE 212-496-8
PubChem 69972
SMILES
InChI
Apparence gaz
Propriétés chimiques
Formule C4H6  [Isomères]
Masse molaire[2] 54,090 4 ± 0,003 6 g/mol
C 88,82 %, H 11,18 %,
Moment dipolaire 0,132 ± 0,001 D [1]
Propriétés physiques
T° ébullition 1,5-2 °C à 972 hPa[3]
Masse volumique 0,733 g·cm-3 [réf. nécessaire]
Propriétés électroniques
1re énergie d'ionisation 9,43 ± 0,02 eV (gaz)[4]
Unités du SI et CNTP, sauf indication contraire.
modifier 

Le cyclobutène de formule brute C4H6 est le cycloalcène le plus petit après le cyclopropène. Il est utilisé dans l'industrie chimique comme monomère dans la synthèse de polymères par polymérisation par ouverture de cycle et comme réactif dans nombre de synthèses organiques.

Synthèse

Le cyclobutène peut être obtenu par élimination sur le 1,2-dibromocyclobutane avec de la poudre de zinc (deshalogénation)[3] :

Il peut être également obtenu par une élimination de Hofmann sur l'hydroxyde de cyclobutyl,triméthyl ammonium conduite par distillation à sec[5] :

En outre, le cyclobutène peut aussi être obtenu par cyclisation photochimique du 1,3-butadiène. Cette méthode fonctionne mais elle a un mauvais rendement[6] :

Finalement, le meilleur rendement de 99,2% de pur cyclobutène est obtenu via la synthèse la plus moderne qui débute du cyclopropylcarbinol, cycloprop-CH2-OH qui est transformé par reflux avec de l'acide chlorhydrique concentré, en cyclobutanol. Celui-ci est tosylé avec le chlorure de tosyle dans la pyridine et finalement ce tosylate, traité à 70 °C avec du t-butylate de potassium, K+(CH3)3CO−, dans le DMSO, fournit le cyclobutène en quantité[7] :

Notes et références

  1. ↑ (en) David R. Lide, Handbook of chemistry and physics, Boca Raton, CRC, , 89e éd., 2736 p. (ISBN 978-1-4200-6679-1 et 1-4200-6679-X), p. 9-50
  2. ↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  3. ↑ a et b R. Willstätter, J. Bruce, Zur Kenntnis der Cyclobutanreihe, Chemische Berichte, 1907, vol. 40, pp. 3979–3999.
  4. ↑ (en) David R. Lide, Handbook of chemistry and physics, Boca Raton, CRC, , 89e éd., 2736 p. (ISBN 978-1-4200-6679-1), p. 10-205
  5. ↑ Hans Beyer, Wolfgang Walter, Organische Chemie, 20e éd., Hirzel Verlag Stuttgart, 1984, p. 364. (ISBN 3-7776-0406-2).
  6. ↑ W. Adam, T. Oppenlaender, G. Zang, The 185-nm photochemistry of cyclobutene and bicyclo[1.1.0]butane, J. Am. Chem. Soc., 1985, vol. 107(13), pp. 3921–3924. DOI 10.1021/ja00299a028
  7. ↑ J. Salaün et A. Fade, Cyclobutene, Org. Synth., 1986, vol. 64, p. 50. DOI 10.15227/orgsyn.064.0050.

Articles connexes


v · m
Alcènes
Diènes
Triènes Cycloheptatriène
Tétraènes

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