- REACTIONS OF DI- AND TRI-TERT-BUTYLCYCLOPENTADIENES WITH DIHALOCARBENES
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Dihalocarbene additions to mixed 1,3- and 1,4-di-tert-butylcyclopentadienes (1, 3) allow to prepare 1,3-di-tert-butyl-4-halobenzenes (9) in an efficient way.Only the 3,4 double bond is attacked regiospecifically in 1,3,5-tri-tert-butylcyclopentadiene (11) (and also in 1).Totally unexpected main products from 11 are compounds 9 again being formed under fragmentation of a tert-butyl group.Only small amounts of 1,2,4-tri-tert-butyl-5-halobenzenes (13, X=Cl, Br) are obtained from 11.A labile primary dichlorocarbene adduct to 11 (12a) can be isolated.Its thermal decomposition occurs with the loss of one tert-butyl group to yield 9a.Base catalyzed degradation of 12a gives 9a and 13a as by-product.
- Dehmlow, Eckehard V.,Bollmann, Christof
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p. 3755 - 3758
(2007/10/02)
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- Derivatives of m-di-tert-butylbenzene. Part VI. The preparation of miscellaneous halogenated compounds
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The preparation of seven series of dihalogenated and monohalogenated derivatives of m-di-tert-butylbenzene, comprising twenty three new compounds, is described.
- Koning, Adrianus Jan de
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p. 421 - 425
(2007/10/02)
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