-
5
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-
0000758786
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-
Kulinkovich O.G., Sviridov S.V., Vasilevski D.A., Savchenko A.I., and Pritytskaya T.S. Zh. Org. Khim. 27 (1991) 294
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(1991)
Zh. Org. Khim.
, vol.27
, pp. 294
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-
Kulinkovich, O.G.1
Sviridov, S.V.2
Vasilevski, D.A.3
Savchenko, A.I.4
Pritytskaya, T.S.5
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9
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37649007525
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-
For reviews see:
-
-
-
-
13
-
-
37649005364
-
-
note
-
A modified ate complex mechanism, assuming the formation of octahedral titanium intermediates, was proposed recently for this reaction (see Ref. 6).
-
-
-
-
16
-
-
37648999268
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-
For the formation of trans-1,2-disubstituted cyclopropanols as major products in reactions between esters and alkoxytitanacyclopropane reagents bearing functional substituents, see:
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-
-
-
23
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0037124795
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-
Quan L.G., Kim S.H., Lee J.C., and Cha J.K. Angew. Chem., Int. Ed. 41 (2002) 2160
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(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 2160
-
-
Quan, L.G.1
Kim, S.H.2
Lee, J.C.3
Cha, J.K.4
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24
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-
0036317694
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Racouchot S., Silvestre I., Ollivier J., Kozyrkov Yu.Yu., Pukin A., Kulinkovich O.G., and Salaun J. Eur. J. Org. Chem. (2002) 2160
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(2002)
Eur. J. Org. Chem.
, pp. 2160
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-
Racouchot, S.1
Silvestre, I.2
Ollivier, J.3
Kozyrkov, Yu.Yu.4
Pukin, A.5
Kulinkovich, O.G.6
Salaun, J.7
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25
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-
37649010071
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-
The same regioselectivity was observed in the titanium-mediated couplings of alkenes:
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-
-
-
30
-
-
37649024550
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-
The formation of oxatitanacyclopentane or azatitanacyclopentane intermediates with the metal atom bound to secondary carbon were evidenced in the reactions of alkoxytitanacyclopropane reagents with ketones, imides, N-acylpyrroles as well as nitriles:
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-
-
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35
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34147093658
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Synthesis of β-iodoketones by oxidation of iodide anion by ceric ammonium nitrare (CAN) in the presence of substituted cyclopropyl alcohols was recently reported:
-
Synthesis of β-iodoketones by oxidation of iodide anion by ceric ammonium nitrare (CAN) in the presence of substituted cyclopropyl alcohols was recently reported:. Jiao J., Nguyen L.X., Patterson D.R., and Flowers II R.A. Org. Lett. 9 (2007) 1323
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(2007)
Org. Lett.
, vol.9
, pp. 1323
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-
Jiao, J.1
Nguyen, L.X.2
Patterson, D.R.3
Flowers II, R.A.4
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36
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37649000284
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For the synthesis of β-iodoketons from α,β-unsaturated ketones, see:
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-
-
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40
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-
0029002874
-
-
Stereochemistry of the intermolecular cyclization of the methyl substituted β-zinc propionates in the presence of tert-butyldimethylchlorosilane was studied by Tamaru, et al.:
-
Stereochemistry of the intermolecular cyclization of the methyl substituted β-zinc propionates in the presence of tert-butyldimethylchlorosilane was studied by Tamaru, et al.:. Yasui K., Tanaka S., and Tamaru Y. Tetrahedron 51 (1995) 6881
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(1995)
Tetrahedron
, vol.51
, pp. 6881
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Yasui, K.1
Tanaka, S.2
Tamaru, Y.3
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41
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37649011729
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-
Narasimhan and Patil reported synthesis of a steroid cyclopropyl alcohol, 1-phenylcyclopropanol and the bicyclic cyclopropanol by the reaction between the corresponding β-iodoketons and excess of zinc powder in the presence of trimethylchlorosilane:
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-
-
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44
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33845279644
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Yoshida et al. reported the formation of 1-phenylcyclopropanol as major product when 3-iodo-1-phenylpropan-1-one was converted into the corresponding β-zincketone by the metalation with Zn-Cu couple:
-
Yoshida et al. reported the formation of 1-phenylcyclopropanol as major product when 3-iodo-1-phenylpropan-1-one was converted into the corresponding β-zincketone by the metalation with Zn-Cu couple:. Ochiai H., Nishihara T., Tamaru Y., and Yoshida Z. J. Org. Chem. 53 (1988) 1343
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(1988)
J. Org. Chem.
, vol.53
, pp. 1343
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-
Ochiai, H.1
Nishihara, T.2
Tamaru, Y.3
Yoshida, Z.4
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45
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-
37649000884
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-
note
-
The corresponding saturated ketones (1-10%) were detected as by-products.
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-
-
-
46
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37649021452
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-
note
-
Addition of 2-3 equiv of triethylamine before the aqueous work-up led to TMS-derivative of alcohol 2a.
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-
-
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47
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37649008174
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15 It was reported also that TMSCl could activate zinc dust:
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-
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49
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4243489506
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-
and references cited therein
-
Knochel P., and Singer R.D. Chem. Rev. 93 (1993) 2117 and references cited therein
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(1993)
Chem. Rev.
, vol.93
, pp. 2117
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Knochel, P.1
Singer, R.D.2
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50
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37649013128
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-
note
-
For the analysis of steric interactions in transition states of the intramolecular cyclizations of β-zincesters, see Ref. 15.
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-
-
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51
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-
37649024668
-
-
note
-
For the generation of titanoketone and titanoester intermediates from the corresponding organozinc compounds, see Ref. 17.
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-
-
-
54
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0037424030
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The formation of 1-cyclohexylcyclopropanol from corresponding β-chloroketone under the same conditions has been observed in first by Olliver:
-
The formation of 1-cyclohexylcyclopropanol from corresponding β-chloroketone under the same conditions has been observed in first by Olliver:. Lecornue F., and Ollivier J. Chem. Commun. (2003) 584
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(2003)
Chem. Commun.
, pp. 584
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-
Lecornue, F.1
Ollivier, J.2
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55
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37649011585
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-
note
-
2, and of EtMgBr, see Ref. 23.
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-
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57
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0030930261
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Thorn M.G., Hill J.E., Waratuke S.A., Johnson E.S., Fanwick P.E., and Rothwell I.P. J. Am. Chem. Soc. 119 (1997) 8630
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(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 8630
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-
Thorn, M.G.1
Hill, J.E.2
Waratuke, S.A.3
Johnson, E.S.4
Fanwick, P.E.5
Rothwell, I.P.6
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63
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0001740014
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Grubbs et al. found no deuterium isotope effect on the stereochemistry of an alkenyl ligand cyclization in titanocene alkenyl chlorides:
-
Grubbs et al. found no deuterium isotope effect on the stereochemistry of an alkenyl ligand cyclization in titanocene alkenyl chlorides:. Clawson L., Soto J., Buchwald S.L., Steigerwald M.L., and Grubbs R.H. J. Am. Chem. Soc. 107 (1985) 3377
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(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 3377
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Clawson, L.1
Soto, J.2
Buchwald, S.L.3
Steigerwald, M.L.4
Grubbs, R.H.5
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64
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0000936656
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-
2-1,5-hexadiene revealed ratio of 1.2:1 trans:cis products, and this stereochemical result was attributed to preference for H, rather than for D, to occupy bridging α-agostic position in the transition state of cyclopentane ring closing step:
-
2-1,5-hexadiene revealed ratio of 1.2:1 trans:cis products, and this stereochemical result was attributed to preference for H, rather than for D, to occupy bridging α-agostic position in the transition state of cyclopentane ring closing step:. Piers W.E., and Bercaw J.E. J. Am. Chem. Soc. 112 (1990) 9406
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(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 9406
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-
Piers, W.E.1
Bercaw, J.E.2
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66
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33751351321
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The absence of any kind of bond linking the metal atom and α-hydrogen in titanium alkyl complexes was concluded recently from the computational results. The authors recommended to avoid use the term 'α-agostic bond' and the alternative expression 'α-agostic geometry' was proposed to eliminate possible misunderstanding:
-
The absence of any kind of bond linking the metal atom and α-hydrogen in titanium alkyl complexes was concluded recently from the computational results. The authors recommended to avoid use the term 'α-agostic bond' and the alternative expression 'α-agostic geometry' was proposed to eliminate possible misunderstanding:. Vidal I., Melchor S., Alkorta I., Elguero J., Sundberg M.R., and Dobado J.A. Organometallics 25 (2006) 5638
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(2006)
Organometallics
, vol.25
, pp. 5638
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-
Vidal, I.1
Melchor, S.2
Alkorta, I.3
Elguero, J.4
Sundberg, M.R.5
Dobado, J.A.6
-
72
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37649013414
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For a preferred formation of tetrahedral configuration for zinc and magnesium organometallics in ether solvents see, for example:
-
-
-
-
73
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-
37649014313
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Metallorganische Verbindungen Be, Mg, Ca, Sr, Ba, Zn, Cd
-
Georg Thieme, Stuttgart
-
Metallorganische Verbindungen Be, Mg, Ca, Sr, Ba, Zn, Cd. Methoden der Organischen Chemie (Houben-Weyl) Vol. XII/2a (1973), Georg Thieme, Stuttgart
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(1973)
Methoden der Organischen Chemie (Houben-Weyl)
, vol.XII-2a
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-
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78
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37649022712
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note
-
6 The NMR yields and diastereomer ratios were virtually the same as obtained by standard stoichiometric procedure described in this work.
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-
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79
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-
37649016430
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-
note
-
Control experiment with undeuterated Grignard reagent was also performed under the same conditions.
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