-
2
-
-
0004035157
-
Reactive Intermediates
-
A general review on carbenoid reactions is presented in Abramovitch, R. A., Ed.; Plenum Press: New York
-
A general review on carbenoid reactions is presented in: Wulfman, D. S.; Poling, B. “Reactive Intermediates”; Abramovitch, R. A., Ed.; Plenum Press: New York, 1980, Vol. 1, p 321.
-
(1980)
, vol.1
, pp. 321
-
-
Wulfman, D.S.1
Poling, B.2
-
3
-
-
0021755817
-
-
Recent studies on carbenoid C-H insertion are given in (b) Taber, D. F.; Petty, E. H. J. Org. Chem. 1982, 47, 4808. (c) Taber, D. F.; Raman, K. J. Am. Chem. Soc. 1983, 105, 5935. (d) Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (f) Taber, D. F.; Ruckle, R. E.; Jr. Tetrahedron Lett. 1985, 26, 3059
-
Recent studies on carbenoid C-H insertion are given in: (a) Cane, D. E.; Thomas, P. J. J. Am. Chem. Soc. 1984, 106, 5295. (b) Taber, D. F.; Petty, E. H. J. Org. Chem. 1982, 47, 4808. (c) Taber, D. F.; Raman, K. J. Am. Chem. Soc. 1983, 105, 5935. (d) Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688. (f) Taber, D. F.; Ruckle, R. E.; Jr. Tetrahedron Lett. 1985, 26, 3059.
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(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 5295
-
-
Cane, D.E.1
Thomas, P.J.2
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4
-
-
0002797371
-
-
Recent studies on carbenoid cyclopropanation are found in (b) Doyle, M. P.; van Leusen, D.; Tamblyn, W. H. Synthesis 1981, 787. (c) Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695
-
Recent studies on carbenoid cyclopropanation are found in: (a) Doyle, M. P.; Dorow, R. L.; Buhro, W. E.; Griffin, J. H.; Tamblyn, W. H.; Trudell, M. L. Organometallics 1984, 3, 44. (b) Doyle, M. P.; van Leusen, D.; Tamblyn, W. H. Synthesis 1981, 787. (c) Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695.
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(1984)
Organometallics
, vol.3
, pp. 44
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Doyle, M.P.1
Dorow, R.L.2
Buhro, W.E.3
Griffin, J.H.4
Tamblyn, W.H.5
Trudell, M.L.6
-
5
-
-
0018163936
-
-
Carbenoids have been used for intramolecular X-H insertion (b) Ratcliffe, R. W.; Salzmann, T. N.; Christensen, B. G. Tetrahedron Lett. 1980, 21, 31. (c) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G. Tetrahedron Lett. 1980, 21, 1193. (d) Melillo, D. G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783. (e) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G. Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6163. (f) Yamamoto, S.; Itani, H.; Takahashi, H.; Tsuji, T.; Nagata, W. Tetrahedron Lett. 1984, 25, 4545. (g) Campbell, M. M.; Jasys, V. J. Heterocycles 1981, 16, 1487. (h) Moody, C. J.; Pearson, C. J.; Lawton, G. Tetrahedron Lett. 1985, 26, 3171
-
Carbenoids have been used for intramolecular X-H insertion: (a) Cama, L. D.; Christensen, B. G. Tetrahedron Lett. 1978, 4233. (b) Ratcliffe, R. W.; Salzmann, T. N.; Christensen, B. G. Tetrahedron Lett. 1980, 21, 31. (c) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G. Tetrahedron Lett. 1980, 21, 1193. (d) Melillo, D. G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783. (e) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G. Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6163. (f) Yamamoto, S.; Itani, H.; Takahashi, H.; Tsuji, T.; Nagata, W. Tetrahedron Lett. 1984, 25, 4545. (g) Campbell, M. M.; Jasys, V. J. Heterocycles 1981, 16, 1487. (h) Moody, C. J.; Pearson, C. J.; Lawton, G. Tetrahedron Lett. 1985, 26, 3171.
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(1978)
Tetrahedron Lett.
, pp. 4233
-
-
Cama, L.D.1
Christensen, B.G.2
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6
-
-
0001042424
-
-
A leading reference on intramolecular cyclopropanation with diazo esters is
-
A leading reference on intramolecular cyclopropanation with diazo esters is: Hudlicky, T.; Reddy, D. B.; Govindan, S. V.; Kulp, T.; Still, B.; Sheth, J. P. J. Org. Chem. 1983, 48, 3422.
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(1983)
J. Org. Chem.
, vol.48
, pp. 3422
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Hudlicky, T.1
Reddy, D.B.2
Govindan, S.V.3
Kulp, T.4
Still, B.5
Sheth, J.P.6
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7
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0011441434
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Bright, G. M.; Dee, M. F.; Kellogg, M. S. Heterocycles 1980, 14, 1251.
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(1980)
Heterocycles
, vol.14
, pp. 1251
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Bright, G.M.1
Dee, M.F.2
Kellogg, M.S.3
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8
-
-
0000866402
-
-
Paulissen, R.; Reimlinger, H.; Hayez, E.; Hubert, A. J.; Teyssie, P. Tetrahedron Lett. 1973, 2233.
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(1973)
Tetrahedron Lett.
, pp. 2233
-
-
Paulissen, R.1
Reimlinger, H.2
Hayez, E.3
Hubert, A.J.4
Teyssie, P.5
-
9
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0001449601
-
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Noels, A. F.; Demonceau, A.; Petiniot, N.; Hubert, A. J.; Teyssie, P. Tetrahedron 1982, 38, 2733.
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(1982)
Tetrahedron
, vol.38
, pp. 2733
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Noels, A.F.1
Demonceau, A.2
Petiniot, N.3
Hubert, A.J.4
Teyssie, P.5
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10
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49549150557
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Paulissen, R.; Hayez, E.; Hubert, A. J.; Teyssie, P. Tetrahedron Lett. 1974, 607.
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(1974)
Tetrahedron Lett.
, pp. 607
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Paulissen, R.1
Hayez, E.2
Hubert, A.J.3
Teyssie, P.4
-
12
-
-
33845550021
-
-
2O were found to be better in promoting the insertion
-
2O were found to be better in promoting the insertion. McClure, D. E.; Lumma, P. K.; Arison, B. H.; Jones, J. H.; Baldwin, J. J. J. Org. Chem. 1983, 48, 2675.
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(1983)
J. Org. Chem.
, vol.48
, pp. 2675
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-
McClure, D.E.1
Lumma, P.K.2
Arison, B.H.3
Jones, J.H.4
Baldwin, J.J.5
-
13
-
-
0021321060
-
-
An attempt to accomplish an intramolecular N-H insertion on 2-substituted 1,2-diazetidin-3-ones is described by
-
An attempt to accomplish an intramolecular N-H insertion on 2-substituted 1,2-diazetidin-3-ones is described by: Taylor, E. C.; Davies, H. M. L. J. Org. Chem. 1984, 49, 113.
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(1984)
J. Org. Chem.
, vol.49
, pp. 113
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Taylor, E.C.1
Davies, H.M.L.2
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14
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0001264217
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Blake, J.; Willson, C. D.; Rapoport, H. J. Am. Chem. Soc. 1964, 86, 5293.
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J. Am. Chem. Soc.
, vol.86
, pp. 5293
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Blake, J.1
Willson, C.D.2
Rapoport, H.3
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17
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0000360982
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Yamada, Y.; Ishii, T.; Kimura, M.; Hosaka, K. Tetrahedron Lett. 1981, 22, 1353.
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(1981)
Tetrahedron Lett.
, vol.22
, pp. 1353
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Yamada, Y.1
Ishii, T.2
Kimura, M.3
Hosaka, K.4
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18
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0016022796
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-
(b) Bram, G.; Vilkas, M. Bull. Soc. Chim. Fr. 1964, 945. (c) Bates, H. A.; Rapoport, H. J. Am. Chem. Soc. 1979, 101, 1259
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(a) Cox, M. T.; Jackson, A. H.; Kenner, G. W.; McCombie, S. W.; Smith, K. M. J. Chem. Soc. Perkin Trans. 1 1974, 516. (b) Bram, G.; Vilkas, M. Bull. Soc. Chim. Fr. 1964, 945. (c) Bates, H. A.; Rapoport, H. J. Am. Chem. Soc. 1979, 101, 1259.
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J. Chem. Soc. Perkin Trans. 1
, pp. 516
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Cox, M.T.1
Jackson, A.H.2
Kenner, G.W.3
McCombie, S.W.4
Smith, K.M.5
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21
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0000442218
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(b) Luly, J. R.; Rapoport, H. J. Am. Chem. Soc. 1983, 105, 2859
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(a) Pinnick, H. W.; Chang, Y.-H. J. Org. Chem. 1978, 43, 4662. (b) Luly, J. R.; Rapoport, H. J. Am. Chem. Soc. 1983, 105, 2859.
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J. Org. Chem.
, vol.43
, pp. 4662
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Pinnick, H.W.1
Chang, Y.-H.2
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22
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0015873411
-
Synthesis
-
and references therein (b) Morimoto, A.; Okutani, T.; Masuda, K. Chem. Pharm. Bull. 1973, 21, 228
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(a) Chatterjee, S. S.; Shoeb, A. Synthesis 1973, 153 and references therein. (b) Morimoto, A.; Okutani, T.; Masuda, K. Chem. Pharm. Bull. 1973, 21, 228.
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(1973)
, pp. 153
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Chatterjee, S.S.1
Shoeb, A.2
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23
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0000774152
-
Organic Syntheses
-
Wiley: New York Collect
-
Strube, R. E. “Organic Syntheses”; Wiley: New York, 1963; Collect. Vol. 4, p 417.
-
(1963)
, vol.4
, pp. 417
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Strube, R.E.1
-
24
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84971081622
-
-
and references therein
-
Lengyel, I.; Sheehan, J. C. Angew. Chem., Int. Ed. Engl. 1968, 7, 25 and references therein.
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(1968)
Angew. Chem., Int. Ed. Engl.
, vol.7
, pp. 25
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Lengyel, I.1
Sheehan, J.C.2
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25
-
-
37049121342
-
-
An interesting synthesis of 2-alkyl-3-oxotetrahydrothiophene from 4-(alkylthio)-1-diazobutan-2-one is the only example of a carbenoid reaction used to synthesize any of the heterocycles we have made. This reaction proceeds via intramolecular carbenoid addition to sulfur to give an intermediate cyclic sulfur ylide that then rearranges to the product either via a [2, 3] sigmatropic shift or a Stevens rearrangement, depending upon the alkylthio group
-
An interesting synthesis of 2-alkyl-3-oxotetrahydrothiophene from 4-(alkylthio)-1-diazobutan-2-one is the only example of a carbenoid reaction used to synthesize any of the heterocycles we have made. This reaction proceeds via intramolecular carbenoid addition to sulfur to give an intermediate cyclic sulfur ylide that then rearranges to the product either via a [2,3] sigmatropic shift or a Stevens rearrangement, depending upon the alkylthio group. Kondo, K.; Ojima, I. J. Chem. Soc., Chem. Commun. 1972, 860.
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(1972)
J. Chem. Soc., Chem. Commun.
, pp. 860
-
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Kondo, K.1
Ojima, I.2
-
27
-
-
0001985626
-
-
Another route outlined below employed the Blaise reaction for synthesizing 37; however, we found it less satisfactory than the scheme described in the text. (formula omited)
-
Another route (Bellassoued, M.; Gaudemar, M. J. Organomet. Chem. 1974, 81, 139) outlined below employed the Blaise reaction for synthesizing 37; however, we found it less satisfactory than the scheme described in the text. (formula omited)
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(1974)
J. Organomet. Chem.
, vol.81
, pp. 139
-
-
Bellassoued, M.1
Gaudemar, M.2
-
30
-
-
0003668536
-
Peptide Synthesis
-
For a list of cysteine thiol-protecting groups, see 2nd ed. Wiley New York
-
For a list of cysteine thiol-protecting groups, see: Bodanszky, M.; Klausner, Y. A.; Ondetti, M. A. “Peptide Synthesis”, 2nd ed., Wiley: New York 1976.
-
(1976)
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Bodanszky, M.1
Klausner, Y.A.2
Ondetti, M.A.3
-
31
-
-
0015939993
-
-
A similar procedure to that used to protect cysteine was employed by
-
A similar procedure to that used to protect cysteine was employed by: Erickson, B. W.; Merrifield, R. B. J. Am. Chem. Soc. 1973, 95, 3750.
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(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 3750
-
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Erickson, B.W.1
Merrifield, R.B.2
-
34
-
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0001254944
-
-
4; however, hydrogen sulfide did not react
-
4; however, hydrogen sulfide did not react. Johnson, S. A.; Hunt, H. R.; Neumann, H. M. Inorg. Chem. 1963, 2, 960.
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(1963)
Inorg. Chem.
, vol.2
, pp. 960
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Johnson, S.A.1
Hunt, H.R.2
Neumann, H.M.3
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35
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0003828322
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Chemistry of the Amino Acids
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Wiley: New York 6b: Sifferd, R. H.; Du Vigneaud, V. J. Biol. Chem. 1935, 108, 753. 6c: Fosker, A. P.; Law, H. D. J. Chem. Soc. 1965, 7305. 6d: Reitz, M. S.; Rodwell, V. W. Methods Enzymol. 1971, 17 (Part B), 159
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6a: Greenstein, J. P.; Winitz, M. “Chemistry of the Amino Acids”; Wiley: New York, 1961; Vol. II, p 891. 6b: Sifferd, R. H.; Du Vigneaud, V. J. Biol. Chem. 1935, 108, 753. 6c: Fosker, A. P.; Law, H. D. J. Chem. Soc. 1965, 7305. 6d: Reitz, M. S.; Rodwell, V. W. Methods Enzymol. 1971, 17 (Part B), 159.
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(1961)
, vol.2
, pp. 891
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Greenstein, J.P.1
Winitz, M.2
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36
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0039080545
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Chitwood, J. L.; Gott, P. G.; Martin, J. C. J. Org. Chem. 1971, 36, 2228.
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, vol.36
, pp. 2228
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Chitwood, J.L.1
Gott, P.G.2
Martin, J.C.3
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