Rappe Rearrangement. The origin of cis-stereoselectivity in the conversion of 2,3-dibromo-2-methyl-cyclopropan-1-one to (Z)-but-2-enoic acid. TS1 pathway forming cyclopropanone.
DOI: 10.14469/hpc/11036 Metadata
Created: 2022-08-25 14:00
Last modified: 2025-05-14 08:54
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Description
Mechanistic studies using Gaussian16
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Files
| Filename | Size | Type | Description |
|---|---|---|---|
| TS1.svg | 17KB | image/svg+xml | Scheme for TS1 |
| index.html | 447 | text/html | Root document V1 |
| TS1.svg | 19KB | image/svg+xml | Scheme for TS1, V2 |
| index.html | 407 | text/html | Root document V2 |
Member of collection / collaboration
| DOI | Description |
|---|---|
| 10.14469/hpc/11172 | The Mechanism of the Rappe Rearrangement – a stereochemical investigation using Density Functional Theory. |
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/10987 | Rappe, GS, cyclopropyl ring closure, cis Na.3H2O Def2-TZVPP G = -5770.767341 |
| 10.14469/hpc/11182 | Rappe, GS, cyclopropyl ring closure, cis Na.4H2O, Def2-SVPP, G = -5845.791839 |
| 10.14469/hpc/11186 | Rappe, TS1, cyclopropyl ring closure, cis Na.4H2O Def2-SVPP, G = -5845.760008, IRC, reverse phase |
| 10.14469/hpc/11089 | Rappe, TS1, CF3, cyclopropyl ring closure, cis,, G = -5676.959417 |
| 10.14469/hpc/11088 | Rappe, TS1, cyclopropyl ring closure, trans, Ph, Def2-TZVPP, G = -5570.845733 IRC |
| 10.14469/hpc/11013 | Rappe, TS1, cyclopropyl ring closure, cis Na.4H2O Def2-SVPP G = -5845.760008 DG = 20.0 |
| 10.14469/hpc/11038 | Rappe, GS, cyclopropyl ring closure, Def2-TZVPP, trans enol, G = -5379.178478 |
| 10.14469/hpc/11093 | Rappe, TS1, CF3, cyclopropyl ring closure, trans, G = -5676.947737 DG = 7.3 |
| 10.14469/hpc/11022 | Rappe, GS, cyclopropyl ring closure, cis Na.4H2O Def2-TZVPP G = -5847.205005 |
| 10.14469/hpc/11033 | Rappe, TS1, cyclopropyl ring closure, cis, more substituted enol, Def2-TZVPP, G = -5379.153802 |
| 10.14469/hpc/11193 | Rappe, GS, cyclopropyl ring closure, cis Na.4H2O Def2-TZVPP (G = -5847.205005) from IRC using Def2-SVPP =G = -5847.205426 |
| 10.14469/hpc/11067 | Rappe, TS1, cyclopropyl ring closure,Ph, cis Def2-TZVPP G = -5570.854876 |
| 10.14469/hpc/11087 | Rappe, TS1, cyclopropyl ring closure, trans, Ph, Def2-TZVPP, G = -5570.848659 |
| 10.14469/hpc/11012 | Rappe, TS1, cyclopropyl ring closure, trans, Na.3H2O Def2-TZVPP, G = -5770.731620, DG = 22.4, DDG = 7.4 |
| 10.14469/hpc/11004 | Rappe, TS1b, cyclopropyl ring closure, trans, Def2-TZVPP G = -5379.153314 DG = 6.5 |
| 10.14469/hpc/11032 | Rappe, TS1, cyclopropyl ring closure, trans, more substituted enol,Def2-TZVPP, G = -5379.150285 |
| 10.14469/hpc/11010 | Rappe, TS1, cyclopropyl ring closure, cis, Na.3H2O, Def2-TZVPP, G = -5770.743384 |
| 10.14469/hpc/11041 | Rappe, GS, cyclopropyl ring closure, Def2-TZVPP, cis more substituted enol, G = -5379.179113 |
| 10.14469/hpc/11031 | Rappe, TS1, cyclopropyl ring closure, cis, Na.3H2O Def2-TZVPP, G = -5770.767341, IRC |
| 10.14469/hpc/11069 | Rappe, TS1, cyclopropyl ring closure,Ph, cis, Def2-TZVPP, G = -5570.870641 IRC |
| 10.14469/hpc/11073 | Rappe, TS1, cyclopropyl ring closure,Ph, cis, Def2-TZVPP, G = -5570.858571 |
| 10.14469/hpc/11061 | Rappe, GS for TS1, cyclopropyl ring closure, Ph, Def2-TZVPP, cis enol G = -5570.870641 |
| 10.14469/hpc/11076 | Rappe, TS1, cyclopropyl ring closure, trans, Ph, Def2-TZVPP, G = -5570.845733 |
| 10.14469/hpc/11035 | Rappe, TS1, cyclopropyl ring closure, trans Na.4H2O, Def2-TZVPP, G = -5847.169852 |
| 10.14469/hpc/11176 | Rappe, TS1, cyclopropyl ring closure, cis Na.4H2O Def2-SVPP, TS for rejoining Br, G = -5845.760427 |
| 10.14469/hpc/11180 | Rappe, TS1, cyclopropyl ring closure, cis Na.4H2O Def2-SVPP, TS for rejoining Br, G = -5845.760427 IRC |
| 10.14469/hpc/11042 | Rappe, GS, cyclopropyl ring closure, Def2-TZVPP, trans more substituted enol, G = -5379.177512 |
| 10.14469/hpc/11092 | Rappe, GS, CF3 cyclopropyl ring closure, Def2-TZVPP, cis enol G = -5676.994258 |
| 10.14469/hpc/11030 | Rappe, TS1, cyclopropyl ring closure, cis Na.4H2O, Def2-TZVPP, G = -5847.181856 DG = 14.5 |
| 10.14469/hpc/11023 | Rappe, TS1, cyclopropyl ring closure, trans, Na.3H2O, Def2-TZVPP, G = -5770.731620, DG = 22.4 IRC |
| 10.14469/hpc/11037 | Rappe Rezrrangement, Reactant 2, cyclopropyl ring closure, Def2-TZVPP, cis enol, G = -5379.184488 |
| 10.14469/hpc/10974 | Rappe, TS1, cyclopropyl ring closure, cis, Def2-SVPP, G = -5378.248910, IRC |
| 10.14469/hpc/11009 | Rappe, TS1, cyclopropyl ring closure, cis, Def2-TZVPP, G = -5379.163716 IRC |
| 10.14469/hpc/11011 | Rappe, TS1, cyclopropyl ring closure, trans, Def2-TZVPP, G = -5379.153314, DG = 6.5, IRC |
| 10.14469/hpc/11095 | Rappe rearrangement. Tetramethyl cyclopropyl bromide solvolysis coupled to electrocyclic ring opening, IRC |
| 10.14469/hpc/11039 | Rappe Rearrangement. FAIR Data Table 1. Free energies for Cyclisation of dibromoenols. TS1 |
| 10.14469/hpc/14917 | Rappe rearrangement. TS1c and TS1d |
| 10.14469/hpc/10996 | Rappe, TS1a, cyclopropyl ring closure, cis Def2-TZVPP G = -5379.163716 |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.14469/hpc/11174 | IRC pathways and animations |