Cyclohexynes as intermediates in a novel endo-cyclization of alkynylzincates derived from 5-hexynyl tosylates

Harada, Toshiro; Otani, Takeshi; Oku, Akira

doi:10.1016/s0040-4039(97)00481-4

Cited by 15 publications

(2 citation statements)

References 22 publications

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“…The preparation of (1-cyclopropylidene)alkylzinc reagents was reported in 1995 by reaction of homopropargylic arenesulfonates with Li triorganozincates according to a similar mechanism (Table ) . From 5-hexynyl and 6-heptynyl tosylates, both endo- and exo-cyclization take place, leading to mixtures (Table ) …”

Section: Reactions Of Maas Involving Nucleophile Ligand Transfer Proc...mentioning

confidence: 99%

Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs

2013

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6. Conclusion 7706 Author Information 7706 Biographies 7707 Acknowledgment 7707 Abbreviations Used 7707 References 7708the corresponding allyl-and propargylchromium reagents that further react with a variety of electrophiles to afford the corresponding adducts in high yields. 102 Bu 6 CrLi 3 similarly behaves as a formal two-electron reductant with ketones and esters bearing a leaving group at the α-position to produce enolates that are intercepted with a variety of electrophiles with high selectivities (Table 8). 103 Such enolates are also capable of reacting with oxiranes to afford γand β-hydroxy esters, depending on the Lewis acid used as promoter. 2143.2.2. Two-Electron Transfers from M,Mn-HeteroMAAs (M = Li, MgX). In 1976, Cahiez et al. disclosed the possible reduction in THF of alkenyl bromides or iodides, as well as aryl chlorides or bromides, using i-PrMgCl in the presence of a catalytic amount of MnCl 2 . 215 The authors proposed the in situ formation of unstable i-Pr 3 MnMgCl and its decomposition by β-elimination to H 3 MnMgCl; reaction of the latter with the halide would then afford an unstable Mn(IV) intermediate, able Scheme 23 Scheme 24 Scheme 21 Scheme 22

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Section: Reactions Of Maas Involving Nucleophile Ligand Transfer Proc...mentioning

confidence: 99%

Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs

2013

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“…Alkynylmetal ate complexes such as alkynylboronates , and -zincates are known to react at the β position with simultaneous migration of the ate ligand to the α position. That alkynylmetals (M = Li, Na, K) also exhibit nucleophilic reactivity at the β position was recently disclosed .…”

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confidence: 99%