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Volumn 65, Issue 28, 2009, Pages 5563-5570

The reductive dimerization of some 1,3-dienes and of 1,3,5-cycloheptatriene in the presence of trimethylchlorosilane: a DFT investigation

Author keywords

Alkadiene; Density functional calculations; Dimerization; Electron transfer; Lithium

Indexed keywords

ALKADIENE; LITHIUM; RADICAL; SILANE DERIVATIVE;

EID: 66749129710     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.087     Document Type: Article
Times cited : (5)

References (64)
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    • Polymerization of butadiene in the presence of lithium (Firestone Tire & Rubber Co.) 1959, GB 817695 19590806 Patent;
    • Polymerization of butadiene in the presence of lithium (Firestone Tire & Rubber Co.) 1959, GB 817695 19590806 Patent;
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    • (1960) Chem. Abstr. , vol.54 , pp. 59545
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    • The empirical 'cis rule' concerning the allyl anion has previously been established by some results, see
    • The empirical 'cis rule' concerning the allyl anion has previously been established by some results, see:
  • 19
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    • Lithium is a better reducing agent than sodium (lithium, E°=-3.04 V in water, and -2.99 V in liquid ammonia at -50 °C; sodium, respectively, E°=-2.71 V and -2.59 V), see:
    • Lithium is a better reducing agent than sodium (lithium, E°=-3.04 V in water, and -2.99 V in liquid ammonia at -50 °C; sodium, respectively, E°=-2.71 V and -2.59 V), see:. Wilds A.L.N., and Nelson A. J. Am. Chem. Soc. 75 (1953) 5360-5365
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 5360-5365
    • Wilds, A.L.N.1    Nelson, A.2
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    • Lithium is more reactive than sodium in the Birch reaction, see:
    • Lithium is more reactive than sodium in the Birch reaction, see:. Rabideau P.W. Tetrahedron 45 (1989) 1579-1603
    • (1989) Tetrahedron , vol.45 , pp. 1579-1603
    • Rabideau, P.W.1
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    • The 1,4-addition of tert-butyllithium to 1,3-butadiene led to neopentylallyllithium of similar structure to 6. cis-trans isomerization occurs slowly in THF. By heating at 30 °C and then lowered to -18 °C, extensive cis-trans isomerization occurred in favor of the cis-isomer, see:
    • The 1,4-addition of tert-butyllithium to 1,3-butadiene led to neopentylallyllithium of similar structure to 6. cis-trans isomerization occurs slowly in THF. By heating at 30 °C and then lowered to -18 °C, extensive cis-trans isomerization occurred in favor of the cis-isomer, see:. Glaze W.H., Hanicak J.E., Chaudhuri J., Moore M.L., and Duncan D.P. J. Organomet. Chem. 51 (1973) 13-21
    • (1973) J. Organomet. Chem. , vol.51 , pp. 13-21
    • Glaze, W.H.1    Hanicak, J.E.2    Chaudhuri, J.3    Moore, M.L.4    Duncan, D.P.5
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    • Disilylation of dienes can occur with magnesium metal, see
    • Disilylation of dienes can occur with magnesium metal, see:
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    • For ab initio calculations of cis- and trans-butadiene and some of their ions, see:
    • For ab initio calculations of cis- and trans-butadiene and some of their ions, see:. Hinchliffe A. J. Mol. Struct. 10 (1971) 379-383
    • (1971) J. Mol. Struct. , vol.10 , pp. 379-383
    • Hinchliffe, A.1
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    • Watanabe has shown that lithium naphthalene in THF solution induces the formation of di-isoprene dianion, which gives 2,6-dimethyl-2,6-octadiene and 2,7-dimethyl-2,6-octadiene, in 80% yield while sodium naphthalene in THF-benzene leads to a mixture of 2,3,6-trimethyl-1,5-heptadiene (79, and 2,7-dimethyl-2,6-octadiene 20, in 50% yield. See
    • Watanabe has shown that lithium naphthalene in THF solution induces the formation of di-isoprene dianion, which gives 2,6-dimethyl-2,6-octadiene and 2,7-dimethyl-2,6-octadiene, in 80% yield while sodium naphthalene in THF-benzene leads to a mixture of 2,3,6-trimethyl-1,5-heptadiene (79%) and 2,7-dimethyl-2,6-octadiene (20%) in 50% yield. See:
  • 61


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.