- REACTIONS OF CARBENES WITH DIENE AND POLYENE COMPOUNDS. XII. REACTION OF DIHALOGENOCARBENES WITH trans- AND cis-1,3,5- HEXATRIENES AND 1,3,5-CYCLOHEPTATRIENE
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Dichlorocarbenes and dibromocarbenes add to trans- and cis-1,3,5-hexatrienes and 1,3,5-cycloheptatriene regioselectively at the C1=C2 bond.The relative reactivity of this bond in relation to dichlorocarbene in trans-1,3,5-hexatriene is twice as large while that in 1,3,5-cycloheptatriene is five times lower than in 1,3-butadiene.The obtained data are consistent with the data from quantum-chemical calculations.
- Kostikov, R. R.,Molchanov, A. P.
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p. 912 - 916
(2007/10/02)
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- Studies in the Tricyclooctane Series. VI. Dehydrohalogenation of 8,8-Dihalobicycloocta-2,4-dienes: Plausible Intermediates in the Tricyclooctane-Styrene Conversion
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The dehydrohalogenation of 8,8-dichloro- and 8,8-dibromo-bicycloocta-2,4-diene (4c,d) gives rise to the (E)- and (Z)-isomers of β-t-butoxystyrene (2c).Plausible pathways for the conversion are discussed and evidence in support of bicycloocta-2,4-dienes as intermediates in the conversion is presented.The results support the intervention of halobicycloocta-2,4-dienes in the conversion of tetra- and tri-halo-cis-transoid-cis-tricyclo3,5>octanes (1a-d) to styrenes (2a-c).
- Banwell, Martin G.,Halton, Brian
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p. 2685 - 2691
(2007/10/02)
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