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Journal articles on the topic 'Tiffeneau-Demjanov'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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1

Kohlbacher, Stefan M., Vivien-Sandra Ionasz, Laura Ielo, and Vittorio Pace. "The synthetic versatility of the Tiffeneau–Demjanov chemistry in homologation tactics." Monatshefte für Chemie - Chemical Monthly 150, no. 12 (2019): 2011–19. http://dx.doi.org/10.1007/s00706-019-02514-3.

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Abstract The Tiffeneau–Demjanov rearrangement can be regarded as an interesting alternative to the more common semi-pinacol transposition. It is usually employed for ring extension but, under specific conditions, it can also be used for ring contraction. Compared to other techniques, such as the Demjanov rearrangement or homologations with diazo compounds, the Tiffeneau–Demjanov pathway presents attractive features including high yielding and selective processes. Ring enlargements follow very strict and simple rules, such as the movement of the less substituted carbon and retention of the conf
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2

Chow, Leonie, Melanie McClure, and Jonathan White. "Silicon and tin-directed Tiffeneau–Demjanov reaction." Org. Biomol. Chem. 2, no. 5 (2004): 648–50. http://dx.doi.org/10.1039/b314923d.

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3

Alves, Leandro de C., André L. Desiderá, Kleber T. de Oliveira, Sean Newton, Steven V. Ley, and Timothy J. Brocksom. "A practical deca-gram scale ring expansion of (R)-(−)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1." Organic & Biomolecular Chemistry 13, no. 28 (2015): 7633–42. http://dx.doi.org/10.1039/c5ob00525f.

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A route to enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, an intermediate for terpenoids, has been developed and includes a highly chemo- and regioselective Tiffeneau–Demjanov reaction.
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4

Krasavin, Mikhail, Sergey Chuprun, Dmitry Dar’in, Grigory Kantin та Petr Zhmurov. "α-Diazoacetamides in Sc(OTf)3-Catalyzed Tiffeneau–Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles". Synlett 31, № 04 (2020): 373–77. http://dx.doi.org/10.1055/s-0039-1690047.

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A novel Sc(OTf)3-catalyzed Tiffeneau–Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson’s reagent.
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5

McClure, Melanie, Carl Schiesser, and Jonathan White. "The Silicon-Directed Tiffeneau - Demjanov Reaction: Some Theoretical Studies." Australian Journal of Chemistry 57, no. 9 (2004): 869. http://dx.doi.org/10.1071/ch04077.

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The Tiffeneau–Demjanov chain extension reaction was modelled using the B3LYP/6-31G* basis set for both diazonium and water leaving groups. The chain extension of 12 with the diazonium leaving group occurs with an early transition state, a low activation barrier, and very little participation by the silicon substituent. Chain extension of 15, involving displacement of the less reactive leaving group water, occurs with a later transition state, a significantly higher activation barrier, and with greater participation by the silicon substituent.
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6

Krasavin, Mikhail, Maria Eremeyeva, Daniil Zhukovsky та Dmitry Dar’in. "The Use of α-Diazo-γ-butyrolactams in the Büchner–Curtius–Schlotterbeck Reaction of Cyclic Ketones Opens New Entry to Spirocyclic Pyrrolidones". Synlett 31, № 10 (2020): 982–86. http://dx.doi.org/10.1055/s-0040-1708011.

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The only cyclic α-diazocarbonyl compound employed in the Büchner–Curtius–Schlotterbeck ring expansion of cyclic ketones to date was α-diazo-γ-butyrolactone. Encouraged by the recent success using α-diazo acetamides in related Tiffeneau–Demjanov type ring expansions, we extended this approach to various α-diazo-γ-butyrolactams, which produced, under BF3·OEt2-promoted conditions, spirocyclic seven-membered ketones. These findings substantially enhance the possibilities offered by cyclic α-diazocarbonyl compounds in constructing privileged spirocyclic scaffolds for drug design.
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7

Plutschack, Matthew B., D. Tyler McQuade, Giulio Valenti, and Peter H. Seeberger. "Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe." Beilstein Journal of Organic Chemistry 9 (October 7, 2013): 2022–27. http://dx.doi.org/10.3762/bjoc.9.238.

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We describe the synthesis of 1-amino-2,5-anhydro-D-mannose (“mannitolamine”), a key intermediate to the 7-nitro-1,2,3-benzadiazole conjugate (NBDM), using commercially available fluidic devices to increase the throughput. The approach is the first example of a flow-based Tiffeneau–Demjanov rearrangement. Performing this step in flow enables a ~64-fold throughput enhancement relative to batch. The flow process enables the synthesis to be accomplished three times faster than the comparable batch route. The high throughput enabled the production of larger quantities of the fluorescent fructose tr
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8

Hashimoto, Takuya, Yuki Naganawa, and Keiji Maruoka. "Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring Expansion." Journal of the American Chemical Society 131, no. 18 (2009): 6614–17. http://dx.doi.org/10.1021/ja900941k.

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9

Parrain, Jean-Luc, Gaëlle Chouraqui, Maxime Dousset, Karel Le Jeune та Sylvana Cohen. "Tiffeneau–Demjanov Rearrangement by Using α-Chloro-α-diazoacetate: A Direct Access to α-Chlorinated Medium-Size-Ring Ketones via Ring Enlargement". Synthesis 48, № 15 (2016): 2396–401. http://dx.doi.org/10.1055/s-0035-1561413.

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10

Fattori, Daniela, Sylvie Henry, and Pierre Vogel. "The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo[3.2.1]oct-6-en-2-one to soft electrophiles." Tetrahedron 49, no. 8 (1993): 1649–64. http://dx.doi.org/10.1016/s0040-4020(01)80352-5.

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11

FATTORI, D., S. HENRY, and P. VOGEL. "ChemInform Abstract: The Demjanov and Tiffeneau-Demjanov One-Carbon Ring Enlargements of 2- Aminomethyl-7-oxabicyclo(2.2.1)heptane Derivatives. The Stereo- and Regioselective Additions of 8-Oxabicyclo(3.2.1)oct-6-en-2-one to Soft Electrophiles." ChemInform 24, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199324152.

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12

Chow, Leonie, Melanie McClure, and Jonathan White. "Silicon and Tin-Directed Tiffeneau—Demjanov Reaction." ChemInform 35, no. 28 (2004). http://dx.doi.org/10.1002/chin.200428052.

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13

MARCHAND, A. P., D. RAJAPAKSA, S. P. REDDY, W. H. WATSON, and A. NAGL. "ChemInform Abstract: Tiffeneau-Demjanov Ring Homologations of Two Pentacyclo-(5.4.0.02,6.03,10.05,9)undecane-8,11-diones." ChemInform 21, no. 13 (1990). http://dx.doi.org/10.1002/chin.199013141.

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14

Hashimoto, Takuya, Yuki Naganawa, and Keiji Maruoka. "ChemInform Abstract: Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau-Demjanov-Type Ring Expansion." ChemInform 40, no. 38 (2009). http://dx.doi.org/10.1002/chin.200938062.

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15

Dousset, Maxime, Karel Le Jeune, Sylvana Cohen, Jean-Luc Parrain та Gaelle Chouraqui. "ChemInform Abstract: Tiffeneau-Demjanov Rearrangement by Using α-Chloro-α-diazoacetate: A Direct Access to α-Chlorinated Medium-Size-Ring Ketones via Ring Enlargement." ChemInform 47, № 50 (2016). http://dx.doi.org/10.1002/chin.201650028.

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