Preparation of cyclobutene substituted aromatic hydrocarbons

Details Preparation of cyclobutene substituted aromatic hydrocarbons Preparation of cyclobutene substituted aromatic hydrocarbons

1984-05-21

1986-02-11

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

2604105, 260465R, 260465H, 260544B, 560 80, 560108, 560139, 562405, 562488, 564153, 564155, 564180, 568734, 568632, 568929, 568930, 570129, 570143, 570183, 585 25, 585360, C07C 6730

Patent

active

045700117

ABSTRACT:
The invention is a process for the preparation of an aromatic hydrocarbon with a cyclobutene ring fused to the aromatic hydrocarbon which comprises, dissolving an ortho alkyl halomethyl aromatic hydrocarbon in an inert solvent and pyrolyzing the solution of ortho alkyl halomethyl aromatic hydrocarbon in the inert solvent under conditions such that the ortho alkyl and halomethyl substituents form a cyclobutene ring thereby forming an aromatic hydrocarbon having a fused cyclobutene ring.

REFERENCES:
Loudon et al, J. Amer. Chem. Soc., 91 (27), 7577 (1969).
Schiess et al, Tetrahedron Letters, (46), 4569 (1978).
Boekelheide et al, Tetrahedron Letters, (44), 4245 (1978).
Brown, Pyrolytic Methods in Organic Chemistry, pp. 105-106, Academic Press, N.Y., N.Y. (1980).
Schiess et al, "A Kinetic Study of Pyrolytic Pathways to Benzocyclobutene", Tetrahedron Letters, vol. 23, No. 36, pp. 3665-3668.
Schiess et al, "Formation of Substituted Benzocyclobutenes Through Flash Vacuum Pyrolysis", Tetrahedron Letters, vol. 23, No. 36, pp. 3669-3672.
Hussain et al, "Formation of 1-Chlorobenzocyclobutene, Anthracene or Benzofuran by Flash Vacuum Pyrolysis", Tetrahedron Letters, vol. 24, No. 6, pp. 609-612.

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