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Active Metals by Furstner A

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By Furstner A

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It is important to notc that the ring enlargement from 2 to 3 involves a vinylcyclopropane-cyclopcntenc ling expansion which has also bccn observed for thc lithium salts of 2vinylcyclopropanol systems (311. On the other hand, the rearrangement of 5 to 6 is formally a 2-vinylcyclopropanol ring opening with a proton transfer. To our knowledge this is the first report of such a rearrangcment, although 1-vinylcyclopropanol-cyclobutanonc rearrangements havc becn wcll documented [32]. 2-bis(methylene)cycloalkanc-magnesium (l), followed by an intramolecular cycliLation, generating the spiro intermediate (2).

The use of phosphine ligands significanlly enhanced the reactivity of active copper. In general, the more electron donating the phosphine the more reactive towards oxidative addition was the copper. Also, the rcsulting organocopper reagent was generally more nucleophilic. The general trend of reactivities for phosphine-based copper is P{NMe2)3 > PEt3 > P(CHZNMe2)? > P(cyclohexyl)3 > PBu3 > PPh3 > Diphos > P(OEt)3 as shown in Table 1-21. Phosphites were of little use, but nitrogen-containing phosphine ligands had the advantage that phosphine-containing impurities could be removed by a simplc dilute acid work-up.

Examples of this type of reaction are shown in Table 1-17. 6 Cross-Coupling of Vinyl and Aryl Organozinc Reagents Using a Palladium Catalyst The organozinc can be transmetallated to palladium and the resulting organopalladiuni can subsequently be reacted with vinyl or aryl halides giving the cross-coupled products. - Table 1-15. Reactions of RZnX with allylic halides mediated by CuCN . 2 LiRr. Rx Entry RX I Br(CH2)$02Et Zn' + 3 C e CuCN PLiBr [RCu(CN)ZnX] Products Sy2': Sx2 Allylic halide H ~znx I Yield (%) 96:4 83 97:3 98:2 80 :20 91 94 86 1oo:o 97:3 1oo:o 97:3 87 87 93 86 98:2 95:5 88 94 98:2 88 95:5 95:s 90 89 29 I..?

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