synthesis of 1-Phenyl -1,2-Cyclohexadiene and 1-(2-Bromocyclohex-2-En-1-Yl)Benzene and Wurtz-Like Condensation Products in the reaction of 1-(2,3-Dibromocyclohex-1-En-1-Yl) Benzene with Zinc

Abstract

The base-catalysed elimination of 1-(2-bromocyclohex-2-en-1-yl)benzene 1 and the zinc-catalysed elimination of 1-(2,3-dibromocyclohex-1-en-1-yl)benzene 9 have been used for the synthesis of 1-phenyl-1,2-cyclohexadiene 2; reaction of 9 with zinc in THF resulted in the formation of two isomeric Wurtz-like condensation products 3 and 4, but the reaction of 1 with t-BuOK gave the allene 2.

Keywords

1-phenyl -1 2-cyclohexadiene 1-(2-bromocyclohex-2-en-1-yl) benzene 1-(2,3-dibromocyclohex-1-en-1-yl) benzene zinc

References

(a) Favorski

A.E.

, J. Gen. Chem. USSR (Engl. Transl.) 1936, 6, 720; (b) A. E. Favorski, Bull., Soc. Chem. Fr., 1936, 5, 1727.

(a) Ball

W.J.

, and Landor

S. R.

, Proc. Chem. Soc. Lond., 1961, 143; (b) W. J. Ball and S. R. Landor, J. Chem. Soc., 1962, 2298.

(a) Balcı

, and Jones

W. M.

, J. Am. Chem. Soc., 1980, 102, 7607; (b) M. Balcı and W. M. Jones, J. Am. Chem. Soc., 1981, 103, 2874.

(a) Sütbeyaz

, Ceylan

, and Seçen

, J. Chem. Research (M), 1993, 2189; (b) Y. Sütbeyaz, M. Ceylan and H. Seçen, J. Chem. Research (S); 1993, 293.

Tolbert

L.M.

, Slam

MD.N. I.

, Johnson

R. P.

, Loislli

P. M.

, and Shakespeare

W. C.

, J. Am. Chem. Soc., 1990, 112, 6416.

Taskesenligil

, Tümer

, Balcı

, Tr. J. Chem., 1995, 19, 305.

(a) Ceylan

, Seçen

, Sütbeyaz

, J. Chem. Research (M)., 1997, 70; (b) M. Ceylan, H. Seçen, Y. Sütbeyaz, J. Chem. Research (S)., 1997, 501.

Ceylan

, and Budak

, J. Chem. Research (S)., 2001, 368.

Clifford

, Utermoehlen

M. S.

, and Roland

, Lehr ., J. Org. Chem., 1987, 52, 5574.

10.

Garbisch

E.W.

Jr. , J. Org. Chem. 1961, 26, 4165.

11.

Yin

, Abboud

K. A.

, and Jones

W. M.

, J. Am. Chem. Soc., 1993, 115, 8859.

12.

Sonnenberg

, and Winstein

, J. Org. Chem., 1962, 27, 748.

13.

Kitahonoki

, Takano

, Matsuura

, Kotera

, Tetrahedron, 1969, 25, 335.

14.

Crips

G.T.

, and Papadopoulos

, Aust. J. Chem., 1988, 41, 1711.

15.

Pouchert

C.J.

, The Aldrich Library of NMR Spectra, 2nd edn, 1983, 1, 762C.

16.

Pouchert

C.J.

, The Aldrich Library of NMR Spectra, 2nd edn, 1983, 1, 755A.

17.

Wittig

, and Fritze

, Liebigs Ann. Chem., 1968, 711, 82.

18.

Lide

D.R.

, Ph. D., CRC, Handbook of Chemistry and Physics 72nd edn, 1991–1992, 3–331, CRC Press, Inc.

Boston