Debroy, Paromita ; Roy, Sujit (2003) Synthesis of ferrocenes with ene-terminus via water-promoted Barbier-like carbonyl allylation using bimetallic copper(II)/tin(II) reagent Journal of Organometallic Chemistry, 675 (1-2). pp. 105-112. ISSN 0022-328X
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00223...
Related URL: http://dx.doi.org/10.1016/S0022-328X(03)00205-5
Abstract
Barbier-type γ-regiospecific allylation of formylferrocene (1) with allyl bromides in the presence of stannous chloride dihydrate and catalytic cupric chloride in dichloromethane-water (1:1) afforded corresponding ferrocenyl dienes FcCHC(R1)C(R2)CH2 (3-6). On the other hand, similar reactions of 1,1'-bis-formylferrocene (2) yielded oxa-bridged [3]-ferrocenophanes having allyl pendants Fc[CH2C(R2)CH(R1)CH-μ (O)-CHCH(R1)C(R2)CH2] (8-11). The latter appear to result from the dehydration of intermediate homoallylic alcohols. Dehydration could be arrested in case of reaction of 1 and 2 with 1-bromo-3-methyl-but-2-ene, which results in the formation of homoallylic alcohols FcCH(OH)C(Me2)CHCH2 (7) and Fc[CH(OH)C(Me2)CHCH2]2 (12), respectively. All the reactions completely fail in absence of water.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Alkenylferrocene; 1,3-Butadienylferrocene; [3]-Oxa-ferrocenophane; Allyltin; Allylation |
| ID Code: | 42944 |
| Deposited On: | 08 Jun 2011 08:12 |
| Last Modified: | 08 Jun 2011 08:12 |
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