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Volumn 13, Issue 15, 2007, Pages 4293-4311

Selective synthesis and reactivity of η5- arylcyclohexadienyliron complexes

Author keywords

Cations; Iron; Nucleophilic addition; Regioselectivity; Synthetic methods

Indexed keywords

NUCLEOPHILES; REGIOSELECTIVITY; SPECTROSCOPIC ANALYSIS; STABILIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 34250318467     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601513     Document Type: Article
Times cited : (17)

References (136)
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    • This type of strategy is generally applicable with a wide range of carbonylmetal complexes. For examples of recent developments, see;
    • This type of strategy is generally applicable with a wide range of carbonylmetal complexes. For examples of recent developments, see;
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    • The original preparations of phenylcyclohexadienyliron complexes by conventional methods employing hydride abstraction required Chromatographic separation of the precursor diene complexes and, in the 2-phenyl case, gave the product only as the minor component of a mixture with the 3-phenyl regioisomer. The lack of easily scalable regioselective access to these salts has held back the development of their use as intermediates in organic synthesis. Preparations of phenylcyclohexadienyliron tetrafluroborate salts; a T. H. Whitesides, J. P. Nielan, J. Am. Chem. Soc. 1976, 98, 66-73;
    • The original preparations of phenylcyclohexadienyliron complexes by conventional methods employing hydride abstraction required Chromatographic separation of the precursor diene complexes and, in the 2-phenyl case, gave the product only as the minor component of a mixture with the 3-phenyl regioisomer. The lack of easily scalable regioselective access to these salts has held back the development of their use as intermediates in organic synthesis. Preparations of phenylcyclohexadienyliron tetrafluroborate salts; a) T. H. Whitesides, J. P. Nielan, J. Am. Chem. Soc. 1976, 98, 66-73;
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    • III procedure, see: a) G. R. Stephenson, J. Chem. Soc. Perkin Trans. 1 1982, 2449-2456;
    • III procedure, see: a) G. R. Stephenson, J. Chem. Soc. Perkin Trans. 1 1982, 2449-2456;
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    • Relative to the directing substituent, ipso refers to addition at the site of substitution, a refers to addition beside the substituent, and to refers to addition at the end of the it system remote from the substituent. This labeling system has recently been discussed in detail and extended to allow internal nucleophile addition to be described: G. R. Stephenson. Polyfunctional Electrophilic Multihapto-organometallics for Organic Synthesis in Handbook of Functionalised Organometallics Ed, P. Knochel, Wiley-VCH, Weinheim, 2005, pp. 569-626. In cases where more than one unsymmetrically placed substituent exerts a directing effect, if both substituents promote nucleophile addition at the same position in the π system, this is termed mutually reinforcing, otherwise the directing groups are described as opposed
    • Relative to the directing substituent, ipso refers to addition at the site of substitution, a refers to addition beside the substituent, and to refers to addition at the end of the it system remote from the substituent. This labeling system has recently been discussed in detail and extended to allow internal nucleophile addition to be described: G. R. Stephenson. "Polyfunctional Electrophilic Multihapto-organometallics for Organic Synthesis" in Handbook of Functionalised Organometallics (Ed.: P. Knochel). Wiley-VCH, Weinheim, 2005, pp. 569-626. In cases where more than one unsymmetrically placed substituent exerts a directing effect, if both substituents promote nucleophile addition at the same position in the π system, this is termed "mutually reinforcing", otherwise the directing groups are described as "opposed".
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    • A recent critique has suggested that the reactivity-selectivity principle may not be generally applicable, but the authors conclude that a decrease in selectivity with increasing reactivity can be expected in the case of fast reactions that are close to the diffusion control limit so the principle is most likely to be valid when applied to highly reactive cationic electrophiles: H. O. Mayr, A. R. Ofial, Angew. Chem. 2006, 118, 1876-1886;
    • A recent critique has suggested that the reactivity-selectivity principle may not be generally applicable, but the authors conclude that a decrease in selectivity with increasing reactivity can be expected in the case of fast reactions that are close to the diffusion control limit so the principle is most likely to be valid when applied to highly reactive cationic electrophiles: H. O. Mayr, A. R. Ofial, Angew. Chem. 2006, 118, 1876-1886;
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    • Methoxidc has also been shown to add at the ω position, see ref, 14
    • Methoxidc has also been shown to add at the ω position, see ref. [14].
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    • a) Crinine is an inhibitor of [3H]citalopram binding to the rat brain serotonin re-uptake transport protein: E. E. Elgorashi, G. I. Stafford, A. K. Jager, J. van Staden. Planta Med. 2006, 72, 470-473. For examples of syntheses of crinine, see:
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.