-
1
-
-
67650277718
-
-
For reviews on Meldrum's acid, see:
-
For reviews on Meldrum's acid, see:
-
-
-
-
5
-
-
67650278882
-
-
Meldrum's acid derivatives are potent electrophiles when disubstituted at the 5-position (quaternized Meldrum's acids) and react with organolithium reagents in an inter- and intramolecular fashion, see:
-
Meldrum's acid derivatives are potent electrophiles when disubstituted at the 5-position (quaternized Meldrum's acids) and react with organolithium reagents in an inter- and intramolecular fashion, see:
-
-
-
-
7
-
-
37049077339
-
-
Mahidol C., Pinyopronpanit Y., Radviroongit S., Thebtaranonth C., and Thebtaranonth Y. J. Chem. Soc., Chem. Commun. (1988) 1382-1383
-
(1988)
J. Chem. Soc., Chem. Commun.
, pp. 1382-1383
-
-
Mahidol, C.1
Pinyopronpanit, Y.2
Radviroongit, S.3
Thebtaranonth, C.4
Thebtaranonth, Y.5
-
10
-
-
31144465775
-
-
Fillion E., Dumas A.M., Kuropatwa B.A., Malhotra N.R., and Sitler T.C. J. Org. Chem. 71 (2006) 409-412
-
(2006)
J. Org. Chem.
, vol.71
, pp. 409-412
-
-
Fillion, E.1
Dumas, A.M.2
Kuropatwa, B.A.3
Malhotra, N.R.4
Sitler, T.C.5
-
13
-
-
67650278393
-
-
A limited number of intramolecular electrophilic aromatic substitution reactions of arenes with 5-alkylidene Meldrum's acid derivatives promoted by protic acids have also been described, see:
-
A limited number of intramolecular electrophilic aromatic substitution reactions of arenes with 5-alkylidene Meldrum's acid derivatives promoted by protic acids have also been described, see:
-
-
-
-
16
-
-
67650274863
-
-
Protic acid-promoted intramolecular Friedel-Crafts acylation with acyl Meldrum's acid derivatives were reported. Mechanistic evidences suggested a protonated acyl Meldrum's acid as the acylating agent, instead of a ketene or protonated ketene species, see:
-
Protic acid-promoted intramolecular Friedel-Crafts acylation with acyl Meldrum's acid derivatives were reported. Mechanistic evidences suggested a protonated acyl Meldrum's acid as the acylating agent, instead of a ketene or protonated ketene species, see:
-
-
-
-
17
-
-
5644289358
-
-
Xu F., Armstrong III J.D., Zhou G.X., Simmons B., Hughes D., Ge Z., and Grabowski E.J.J. J. Am. Chem. Soc. 126 (2004) 13002-13009
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13002-13009
-
-
Xu, F.1
Armstrong III, J.D.2
Zhou, G.X.3
Simmons, B.4
Hughes, D.5
Ge, Z.6
Grabowski, E.J.J.7
-
18
-
-
67650276935
-
-
Formation of 2-(3-oxoacyl)pyrroles through Friedel-Crafts acylation of pyrrole with acylated Meldrum's acids, see:
-
Formation of 2-(3-oxoacyl)pyrroles through Friedel-Crafts acylation of pyrrole with acylated Meldrum's acids, see:
-
-
-
-
19
-
-
0000250492
-
-
Cantín A., Moya P., Miranda M.A., Primo J., and Primo-Yúfera E. J. Agric. Food Chem. 46 (1998) 4748-4753
-
(1998)
J. Agric. Food Chem.
, vol.46
, pp. 4748-4753
-
-
Cantín, A.1
Moya, P.2
Miranda, M.A.3
Primo, J.4
Primo-Yúfera, E.5
-
21
-
-
41149101973
-
-
For a review of the use of Meldrum acids in the synthesis of natural products, see:
-
For a review of the use of Meldrum acids in the synthesis of natural products, see:. Ivanov A.S. Chem. Soc. Rev. 37 (2008) 789-811
-
(2008)
Chem. Soc. Rev.
, vol.37
, pp. 789-811
-
-
Ivanov, A.S.1
-
24
-
-
0000823558
-
-
Meldrum stated that the treatment of 2,2-dimethyl-1,3-dioxin-4,6-dione with excess of alkali 'was found to cause disruption into acetone and malonic acid'. However, no experimental data was provided, see:
-
Meldrum stated that the treatment of 2,2-dimethyl-1,3-dioxin-4,6-dione with excess of alkali 'was found to cause disruption into acetone and malonic acid'. However, no experimental data was provided, see:. Meldrum A.N. J. Chem. Soc. 93 (1908) 598-601
-
(1908)
J. Chem. Soc.
, vol.93
, pp. 598-601
-
-
Meldrum, A.N.1
-
33
-
-
67650276592
-
-
The competitive reaction of an equimolar mixture of t-BuOH and EtOH with Meldrum's acid at reflux furnished a 1:3.8 ratio of the corresponding esters, see:
-
The competitive reaction of an equimolar mixture of t-BuOH and EtOH with Meldrum's acid at reflux furnished a 1:3.8 ratio of the corresponding esters, see:
-
-
-
-
35
-
-
67650272270
-
-
The competitive reaction of an equimolar mixture of t-BuOH and n-pentanol with acetylketene revealed a 8.2:1 selectivity favoring the less sterically demanding 1° alcohol, see
-
The competitive reaction of an equimolar mixture of t-BuOH and n-pentanol with acetylketene revealed a 8.2:1 selectivity favoring the less sterically demanding 1° alcohol, see:
-
-
-
-
37
-
-
67650276245
-
-
2O/DMF, see:
-
2O/DMF, see:
-
-
-
-
40
-
-
67650276246
-
-
2O/pyridine, see:
-
2O/pyridine, see:
-
-
-
-
42
-
-
67650278569
-
-
2O/2-pentanone, see:
-
2O/2-pentanone, see:
-
-
-
-
44
-
-
67650274862
-
-
Alcohols as solvent, see
-
Alcohols as solvent, see:
-
-
-
-
47
-
-
0020682790
-
-
Chorev M., Rubini E., Gilon C., Wormser U., and Selinger Z. J. Med. Chem. 26 (1983) 129-135
-
(1983)
J. Med. Chem.
, vol.26
, pp. 129-135
-
-
Chorev, M.1
Rubini, E.2
Gilon, C.3
Wormser, U.4
Selinger, Z.5
-
48
-
-
67650278390
-
-
Reaction with phenols, see
-
Reaction with phenols, see:
-
-
-
-
50
-
-
67650275170
-
-
Formation of amide under neutral conditions has been also reported, see
-
Formation of amide under neutral conditions has been also reported, see:
-
-
-
-
53
-
-
0035700775
-
-
Carotti A., Carrieri A., Cellamare S., Fanizzi F.P., Gavuzzo E., and Mazza F. Biopolymers 60 (2001) 322-332
-
(2001)
Biopolymers
, vol.60
, pp. 322-332
-
-
Carotti, A.1
Carrieri, A.2
Cellamare, S.3
Fanizzi, F.P.4
Gavuzzo, E.5
Mazza, F.6
-
54
-
-
67650275579
-
-
For reviews, see
-
For reviews, see:
-
-
-
-
59
-
-
0141551130
-
-
Baxter G.J., Brown R.F.C., Eastwood F.W., Gatehouse B.M., and Nesbit M.C. Aust. J. Chem. 31 (1978) 1757-1767
-
(1978)
Aust. J. Chem.
, vol.31
, pp. 1757-1767
-
-
Baxter, G.J.1
Brown, R.F.C.2
Eastwood, F.W.3
Gatehouse, B.M.4
Nesbit, M.C.5
-
60
-
-
67650278035
-
-
For ab initio studies on the formation of ketenes via pyrolysis of Meldrum's acid derivatives, see:
-
For ab initio studies on the formation of ketenes via pyrolysis of Meldrum's acid derivatives, see:
-
-
-
-
62
-
-
0000847519
-
-
Matsui H., Zückerman E.J., Katagiri N., Kaneko C., Ham S., and Birney D.M. J. Phys. Chem. A 101 (1997) 3936-3941
-
(1997)
J. Phys. Chem. A
, vol.101
, pp. 3936-3941
-
-
Matsui, H.1
Zückerman, E.J.2
Katagiri, N.3
Kaneko, C.4
Ham, S.5
Birney, D.M.6
-
64
-
-
0000589131
-
-
2AlCl with oximinosulfonate Meldrum's acid derivatives, see:
-
2AlCl with oximinosulfonate Meldrum's acid derivatives, see:. Renslo A.R., and Danheiser R.L. J. Org. Chem. 63 (1998) 7840-7850
-
(1998)
J. Org. Chem.
, vol.63
, pp. 7840-7850
-
-
Renslo, A.R.1
Danheiser, R.L.2
-
68
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-
0012266139
-
-
2. In addition, attack at the ortho position is hindered as the para/ortho ratio is 0.6 for toluene and 6.7 for tert-butyl benzene, see:
-
2. In addition, attack at the ortho position is hindered as the para/ortho ratio is 0.6 for toluene and 6.7 for tert-butyl benzene, see:. Masci B. Tetrahedron 45 (1989) 2719-2730
-
(1989)
Tetrahedron
, vol.45
, pp. 2719-2730
-
-
Masci, B.1
-
69
-
-
20044390256
-
-
For a review on gem-disubstituted effect, see:
-
For a review on gem-disubstituted effect, see:. Jung M.E., and Piizzi G. Chem. Rev. 105 (2005) 1735-1766
-
(2005)
Chem. Rev.
, vol.105
, pp. 1735-1766
-
-
Jung, M.E.1
Piizzi, G.2
-
70
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67650278880
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-
Intramolecular arylation of ketenium ions, see
-
Intramolecular arylation of ketenium ions, see:
-
-
-
-
72
-
-
67650278391
-
-
Intramolecular Friedel-Crafts acylation with chromium-carbene complex-derived ketenes catalyzed by ZnCl2, see
-
2, see:
-
-
-
-
74
-
-
67650278034
-
-
note
-
The plot of the log(data) versus time was linear.
-
-
-
-
76
-
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0003467672
-
-
Wiley-Interscience, New York, NY pp 585-586
-
March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. (1992), Wiley-Interscience, New York, NY pp 585-586
-
(1992)
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed.
-
-
March, J.1
-
77
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67650268788
-
-
Related studies of the thermal decomposition of 2,2,6-trimethyl-4H-1,3-dioxin-4-one have been reported with both kinetics experiments, see:
-
Related studies of the thermal decomposition of 2,2,6-trimethyl-4H-1,3-dioxin-4-one have been reported with both kinetics experiments, see:
-
-
-
-
78
-
-
33845184134
-
-
and ab initio calculations, see:
-
Clemens R.J. J. Am. Chem. Soc. 111 (1989) 2186-2193 and ab initio calculations, see:
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 2186-2193
-
-
Clemens, R.J.1
-
79
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0000247598
-
-
This compound decomposes to acetylketene and reacts just as described for acyl ketenes. These dioxinones do not require the initial enolization step, but still involve a retro hetero-Diels-Alder and acylation step. The rate-determining step in these reactions was determined to be a reversible, unimolecular loss of acetone to provide the reactive intermediate. It was also concluded that since the decomposition of 2,2,6-trimethyl-4H-1,3-dioxin-4-one is reversible, acetone is a competitor with other trapping reagents
-
Birney D.M., and Wagenseller P.E. J. Am. Chem. Soc. 116 (1994) 6262-6270 This compound decomposes to acetylketene and reacts just as described for acyl ketenes. These dioxinones do not require the initial enolization step, but still involve a retro hetero-Diels-Alder and acylation step. The rate-determining step in these reactions was determined to be a reversible, unimolecular loss of acetone to provide the reactive intermediate. It was also concluded that since the decomposition of 2,2,6-trimethyl-4H-1,3-dioxin-4-one is reversible, acetone is a competitor with other trapping reagents
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 6262-6270
-
-
Birney, D.M.1
Wagenseller, P.E.2
-
80
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67650278879
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-
note
-
Similar inhibition by the 1-indanone product was postulated but not experimentally demonstrated.
-
-
-
-
81
-
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67650278036
-
-
note
-
The stability of acyl ketenes, generated through retro hetero-Diels-Alder of Meldrum's acids, is enhanced by increasing the size of the substituent at the 5-position, see Ref. 18.
-
-
-
-
82
-
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0036399737
-
-
3 by Friedel-Crafts acylation product, see:
-
3 by Friedel-Crafts acylation product, see:. Barrett A.G.M., Bouloc N., Braddock D.C., Chadwick D., and Henderson D.A. Synlett (2002) 1653-1656
-
(2002)
Synlett
, pp. 1653-1656
-
-
Barrett, A.G.M.1
Bouloc, N.2
Braddock, D.C.3
Chadwick, D.4
Henderson, D.A.5
-
83
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67650279241
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-
Examples of tautomerization of 1,3-dicarbonyl compounds by lanthanide triflates, see
-
Examples of tautomerization of 1,3-dicarbonyl compounds by lanthanide triflates, see:
-
-
-
-
85
-
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21844460830
-
-
Zhang J., Blazecka P.G., Angell P., Lovdahl M., and Curran T.T. Tetrahedron 61 (2005) 7807-7813
-
(2005)
Tetrahedron
, vol.61
, pp. 7807-7813
-
-
Zhang, J.1
Blazecka, P.G.2
Angell, P.3
Lovdahl, M.4
Curran, T.T.5
-
87
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0034050738
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Yang D., Ye X.-Y., Xu M., Pang K.-W., and Cheung K.-K. J. Am. Chem. Soc. 122 (2000) 1658-1663
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(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 1658-1663
-
-
Yang, D.1
Ye, X.-Y.2
Xu, M.3
Pang, K.-W.4
Cheung, K.-K.5
-
90
-
-
67650278878
-
-
3-catalyzed Friedel-Crafts acylation with acid chlorides and anhydrides, see:
-
3-catalyzed Friedel-Crafts acylation with acid chlorides and anhydrides, see:
-
-
-
-
91
-
-
0037189824
-
-
Picot A., Répichet S., Le Roux C., Dubac J., and Roques N. J. Fluorine Chem. 116 (2002) 129-134
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(2002)
J. Fluorine Chem.
, vol.116
, pp. 129-134
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-
Picot, A.1
Répichet, S.2
Le Roux, C.3
Dubac, J.4
Roques, N.5
-
93
-
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67650268787
-
-
note
-
At fixed time intervals, aliquots were drawn from the reaction mixture and immediately quenched in a triethylamine/methylene chloride solution. These samples were then filtered through plugs of silica, and then injected into a GC equipped with a flame ionization detector. The progression of the reaction was judged by the simple percent conversion as determined by the direct comparison of integration areas of the starting material with the product. Since no internal standard was used in the analysis, percent yields were not determined. All other reaction and analysis conditions were identical between each Lewis acid.
-
-
-
-
94
-
-
67650271877
-
-
note
-
For a large-scale synthesis, the removal of the acetone by-product by reduced pressure could be expected to accelerate the reaction, but this was not explored in this study.
-
-
-
-
95
-
-
3142757194
-
-
2 was prepared according to:
-
2 was prepared according to:. Earle M.J., Hakala U., McAuley B.J., Nieuwenhuyzen M., Ramani A., and Seddon K.R. Chem. Commun. (2004) 1368-1369
-
(2004)
Chem. Commun.
, pp. 1368-1369
-
-
Earle, M.J.1
Hakala, U.2
McAuley, B.J.3
Nieuwenhuyzen, M.4
Ramani, A.5
Seddon, K.R.6
-
96
-
-
67650276244
-
-
note
-
2 has been shown to be effective catalysts for the Friedel-Crafts acylation of 42, see Ref. 4a.
-
-
-
-
98
-
-
67650276934
-
-
For examples of Friedel-Crafts acylation catalyzed by lanthanide bis(trifluoromethanesulfonate)amides, see
-
For examples of Friedel-Crafts acylation catalyzed by lanthanide bis(trifluoromethanesulfonate)amides, see:
-
-
-
-
100
-
-
1542485845
-
-
Mikami K., Kotera O., Motoyama Y., Sakaguchi H., and Maruta M. Synlett (1996) 171-172
-
(1996)
Synlett
, pp. 171-172
-
-
Mikami, K.1
Kotera, O.2
Motoyama, Y.3
Sakaguchi, H.4
Maruta, M.5
-
101
-
-
67650279240
-
-
2NH, see:
-
2NH, see:
-
-
-
-
108
-
-
67650275899
-
-
2O, see:
-
2O, see:
-
-
-
-
110
-
-
67650271876
-
-
See also
-
See also:
-
-
-
-
111
-
-
33749000858
-
-
Rosenfeld D.C., Shekhar S., Takemiya A., Utsunomiya M., and Hartwig J.F. Org. Lett. 8 (2006) 4179-4182
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(2006)
Org. Lett.
, vol.8
, pp. 4179-4182
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-
Rosenfeld, D.C.1
Shekhar, S.2
Takemiya, A.3
Utsunomiya, M.4
Hartwig, J.F.5
-
112
-
-
67650256653
-
-
3 and MeOH, see:
-
3 and MeOH, see:
-
-
-
-
114
-
-
0030581392
-
-
Castellani C.S., Carugo O., Leopizzi C., Perotti A., Invernizzi A.G., and Vidari G. Tetrahedron 52 (1996) 11045-11052
-
(1996)
Tetrahedron
, vol.52
, pp. 11045-11052
-
-
Castellani, C.S.1
Carugo, O.2
Leopizzi, C.3
Perotti, A.4
Invernizzi, A.G.5
Vidari, G.6
-
115
-
-
67650278032
-
-
13C NMR, see:
-
13C NMR, see:
-
-
-
-
118
-
-
0037653572
-
-
NMR studies of lanthanide triflimidates, see:
-
NMR studies of lanthanide triflimidates, see:. Barbier-Beaudry D., Dormond A., Duris F., Bernard J.M., and Desmurs J.R. J. Fluorine Chem. 121 (2003) 233-238
-
(2003)
J. Fluorine Chem.
, vol.121
, pp. 233-238
-
-
Barbier-Beaudry, D.1
Dormond, A.2
Duris, F.3
Bernard, J.M.4
Desmurs, J.R.5
-
119
-
-
67650278033
-
-
note
-
3 despite the extreme measures taken to dry the catalyst.
-
-
-
-
120
-
-
33751157649
-
-
3-catalyzed aldol reactions with formaldehyde in water, the formation of TfOH was negligible and found not to be an active catalytic species, see:
-
3-catalyzed aldol reactions with formaldehyde in water, the formation of TfOH was negligible and found not to be an active catalytic species, see:. Kobayashi S., and Hachiya I. J. Org. Chem. 59 (1994) 3590-3596
-
(1994)
J. Org. Chem.
, vol.59
, pp. 3590-3596
-
-
Kobayashi, S.1
Hachiya, I.2
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121
-
-
67650278877
-
-
Crooy P., De Neys R., Eliaers J., Livegns R., Simonet G., and Vandevelde J. Bull. Soc. Chim. Belg. 86 (1997) 995-1002
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(1997)
Bull. Soc. Chim. Belg.
, vol.86
, pp. 995-1002
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-
Crooy, P.1
De Neys, R.2
Eliaers, J.3
Livegns, R.4
Simonet, G.5
Vandevelde, J.6
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