All Outputs (45)

Syntheses of 7-substituted anthra[2,3-b]thiophene derivatives and naphtho[2,3-b:6,7-b’]dithiophene (2018)
Journal Article
Al-jumaili, M. A., & Woodward, S. (2018). Syntheses of 7-substituted anthra[2,3-b]thiophene derivatives and naphtho[2,3-b:6,7-b’]dithiophene. Journal of Organic Chemistry, 83(18), 11437-11445. https://doi.org/10.1021/acs.joc.8b01770

7-R-anthra[2,3-b]thiophene derivatives (1, R = H, Me, i-Pr, MeO) are prepared in three steps (in average overall yield >50%) starting from (E)-4-RC6H4CH2(HOCH2)C=CI(CH2OH). The latter are commercial or readily prepared from 2-butyne-1,4-diol and ArC... Read More about Syntheses of 7-substituted anthra[2,3-b]thiophene derivatives and naphtho[2,3-b:6,7-b’]dithiophene.

Capturing waste heat energy with charge-transfer organic thermoelectrics (2018)
Journal Article
Dimitrov, V., & Woodward, S. (2018). Capturing waste heat energy with charge-transfer organic thermoelectrics. SYNTHESIS, 50(19), 3833-3842. https://doi.org/10.1055/s-0037-1610208

Electrically conducting organic salts, known for over 60 years, have recently demonstrated new abilities to convert waste heat directly into electrical power via the thermoelectric effect. Multiple opportunities are emerging for new structure-propert... Read More about Capturing waste heat energy with charge-transfer organic thermoelectrics.

Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes (2018)
Journal Article
Robert Garrett, M., Durán-Peña, M. J., Lewis, W., Pudzs, K., Uzulis, J., Mihailovs, I., …Woodward, S. (2018). Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes. Journal of Materials Chemistry C, 6(13), 3403-3409. https://doi.org/10.1039/c8tc00073e

Reaction of elemental sulfur with 2-R1 and 2,8-R1,R2-substituted tetracenes (2) in refluxing DMF affords 5,6,11,12 tetrathiotetracenes (1) in good yields (74-99%) for a range of substituents where R1,R2 are: H,H (a); Me,H (b); MeO,H (c); Ph,H (d); Me... Read More about Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes.

Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group (2017)
Journal Article
Nouch, R., Cini, M., Magre, M., Abid, M., Diéguez, M., Pàmies, O., …Lewis, W. (in press). Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group. Chemistry - A European Journal, https://doi.org/10.1002/chem.201704247

Simple enantioselective synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline-based organocatalysts. Condensation of cyclopentadiene with the acetyl... Read More about Enantioselective synthesis of 6,6-disubstituted pentafulvenes containing a chiral pendant hydroxy group.

Kinetic analysis of Copper(I)/Feringa-Phosphoramidite Catalysed AlEt3 1,4-Addition to Cyclohex-2-en-1-one (2017)
Journal Article
Willcox, D., Nouch, R., Kingsbury, A., Robinson, D., Carey, J. V., Brough, S., & Woodward, S. (in press). Kinetic analysis of Copper(I)/Feringa-Phosphoramidite Catalysed AlEt3 1,4-Addition to Cyclohex-2-en-1-one. ACS Catalysis, https://doi.org/10.1021/acscatal.7b02198

ReactIR studies of mixtures of AlEt3 (A) and cyclohex-2-en-1-one (CX) in Et2O indicate immediate formation of the Lewis acid-base complex (CX.A) at -40 oC (K = 12.0 M-1, ΔGoreact -1.1 kcal mol-1). Copper(I) catalysts, derived from pre-catalytic Cu(OA... Read More about Kinetic analysis of Copper(I)/Feringa-Phosphoramidite Catalysed AlEt3 1,4-Addition to Cyclohex-2-en-1-one.

Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction (2017)
Journal Article
Al-jumaili, M. A., & Woodward, S. (2017). Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction. Tetrahedron, 73(40), https://doi.org/10.1016/j.tet.2017.08.026

Derivatives of 3,4-ethylenedithiothiophene (EDTT) are reported starting from tetrabromothiophene. Selective 2,5-dilithiation followed by reaction with a range of aldehydes gives diols as mixtures of diastereomers. Only the 2 and 5 positions in thioph... Read More about Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction.

Straightforward synthesis of 2- and 2,8-substituted tetracenes (2017)
Journal Article
Woodward, S., Ackermann, M., Ahirwar, S., Burroughs, L., Robert Garrett, M., Ritchie, J., …Woodward, P. (in press). Straightforward synthesis of 2- and 2,8-substituted tetracenes. Chemistry - A European Journal, https://doi.org/10.1002/chem.201701170

A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)- 1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1 = Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C?CCH... Read More about Straightforward synthesis of 2- and 2,8-substituted tetracenes.

Low-cost and sustainable organic thermoelectrics based on low-dimensional molecular metals (2017)
Journal Article
Huewe, F., Steeger, A., Kostova, K., Burroughs, L., Bauer, I., Strohriegl, P., …Pflaum, J. (2017). Low-cost and sustainable organic thermoelectrics based on low-dimensional molecular metals. Advanced Materials, 29(13), 1605682. https://doi.org/10.1002/adma.201605682

More than 70 % of the primary energy consumed world-wide is wasted, mostly as heat below 100 °C[1]. Thermoelectric generators may convert a substantial amount of this energy into electrical power but high production costs and scarcity of efficient th... Read More about Low-cost and sustainable organic thermoelectrics based on low-dimensional molecular metals.

Using titanium complexes to defeat cancer: the view from the shoulders of titans (2017)
Journal Article
Cini, M., Bradshaw, T. D., & Woodward, S. (in press). Using titanium complexes to defeat cancer: the view from the shoulders of titans. Chemical Society Reviews, https://doi.org/10.1039/C6CS00860G

When the first titanium complex with anticancer activity was identified in the 1970s, it was attractive, based on the presence of the dichloride unit in TiCl2Cp2 (Cp = ?-C5H5)2, to assume its mode of biological action was closely aligned with cisplat... Read More about Using titanium complexes to defeat cancer: the view from the shoulders of titans.

Thin film organic thermoelectric generator based on tetrathiotetracene (2017)
Journal Article
Pudsz, K., Vembris, A., Rutkis, M., & Woodward, S. (in press). Thin film organic thermoelectric generator based on tetrathiotetracene. Advanced Electronic Materials, https://doi.org/10.1002/aelm.201600429

Thin films of p- and n- type organic semiconductors for thermo-electrical (TE) applications are produced by doping of tetrathiotetracene (TTT). To obtain p-type material TTT is doped with iodine during vacuum deposition of thin films or by post-depos... Read More about Thin film organic thermoelectric generator based on tetrathiotetracene.

An efficient synthesis of substituted chrysenes (2016)
Journal Article
Eccleshare, L., Selzer, S., & Woodward, S. (2017). An efficient synthesis of substituted chrysenes. Tetrahedron, 58(5), https://doi.org/10.1016/j.tetlet.2016.12.004

Substituted chrysenes have been swiftly synthesised by the 6-endo-dig cyclisation of ethynylnaphthalenes using platinum(II) chloride. Cyclisation precursors were directly prepared from commercially available 2-bromoaldehydes in a telescoped synthetic... Read More about An efficient synthesis of substituted chrysenes.

Diversification of ortho-fused cycloocta-2,5-dien-1-one cores and 8 to 6-Ring conversion by sigma bond C-C cleavage (2016)
Journal Article
Eccleshare, L., Lozada-Rodriguez, L., Cooper, P., Burroughs, L., Ritchie, J., Lewis, W., & Woodward, S. (in press). Diversification of ortho-fused cycloocta-2,5-dien-1-one cores and 8 to 6-Ring conversion by sigma bond C-C cleavage. Chemistry - A European Journal, 22(35), https://doi.org/10.1002/chem.201601970

Sequential treatment of 2-C6H4Br(CHO) with LiC≡CR1 (R1 = SiMe3, tBu), nBuLi, CuBr∙SMe2 and HC≡CCHClR2 [R2 = Ph, 4-CF3Ph, 3-CNPh, 4-(MeO2C)Ph] at -50 oC leads to formation of an intermediate carbanion (Z)-1,2-C6H4{CA(=O)C≡CBR1}{CH=CH(CH–)R2} (4). Low... Read More about Diversification of ortho-fused cycloocta-2,5-dien-1-one cores and 8 to 6-Ring conversion by sigma bond C-C cleavage.

Efficient preparation of TMSCCl2Br and its use in dichlorocyclopropanation of electron deficient alkenes (2016)
Journal Article
Lee, D. S., Durán-Peña, M. J., Burroughs, L., & Woodward, S. (in press). Efficient preparation of TMSCCl2Br and its use in dichlorocyclopropanation of electron deficient alkenes. Chemistry - A European Journal, 2016(22), https://doi.org/10.1002/chem.201600607

The reaction of excess TMSCl and LiCCl2Br at low temperature is a technically simple high yield route to TMSCCl2Br. The latter is a stable source of the dichlorobromomethide carbanion, which undergoes 1,4-addition with cyclic nitroalkenes and (E)-fum... Read More about Efficient preparation of TMSCCl2Br and its use in dichlorocyclopropanation of electron deficient alkenes.

Understanding anionic Chugaev elimination in pericyclic tetracene formation (2016)
Journal Article
Burroughs, L., Ritchie, J., & Woodward, S. (2016). Understanding anionic Chugaev elimination in pericyclic tetracene formation. Tetrahedron, 72(13), https://doi.org/10.1016/j.tet.2016.02.025

The reaction pathway for the formation of tetracenes from the diols 1,2-C6H4(CHOHC?CAr)2 , LiHDMS, CS2 and MeI has been modelled by computational methods at the CBS-QB3 level of theory. Comparison of PhCHOC(=S)YCCPh (Y = S- or SMe) indicates a sligh... Read More about Understanding anionic Chugaev elimination in pericyclic tetracene formation.

Enantiopure titanocene complexes: direct evidence for paraptosis in cancer cells (2016)
Journal Article
Cini, M., Williams, H. E. L., Fay, M. W., Searle, M., Woodward, S., & Bradshaw, T. D. (2016). Enantiopure titanocene complexes: direct evidence for paraptosis in cancer cells. Metallomics, https://doi.org/10.1039/C5MT00297D

Tolerated by normal tissues, anti-cancer therapies based on titanium compounds are limited by low efficacy/selectivity and lack of understanding of their mode(s) of action. In vitro antitumour activity and mode of cell death incurred by enantiopure T... Read More about Enantiopure titanocene complexes: direct evidence for paraptosis in cancer cells.

Tetrathiotetracene thin film morphology and electrical properties (2015)
Journal Article
Pudzs, K., Vembris, A., Busenbergs, J., Rutkis, M., & Woodward, S. (in press). Tetrathiotetracene thin film morphology and electrical properties. Thin Solid Films, 598, https://doi.org/10.1016/j.tsf.2015.11.087

The electrical properties of organic thin films are determined by their chemical constituents and the morphology of the films deposited. In this paper the morphology of vacuum sublimed (7?10-6 mbar) tetrathiotetracene (TTT) thin films is shown to be... Read More about Tetrathiotetracene thin film morphology and electrical properties.

Asymmetric pentafulvene carbometalation-access to enantiopure titanocene dichlorides of biological relevance (2015)
Journal Article
Cini, M., Bradshaw, T. D., Woodward, S., & Lewis, W. (2015). Asymmetric pentafulvene carbometalation-access to enantiopure titanocene dichlorides of biological relevance. Angewandte Chemie International Edition, 54(47), https://doi.org/10.1002/anie.201508034

Unprecedented asymmetric copper-catalyzed addition of ZnEt2 (ZnBu2) to the exocyclic C[DOUBLE BOND]C bond of pentafulvenes C5H4([DOUBLE BOND]CHAr) (Ar=2-MeOPh and related species) results in enantiomerically enriched (up to 93:7 e.r.) cyclopentadieny... Read More about Asymmetric pentafulvene carbometalation-access to enantiopure titanocene dichlorides of biological relevance.

One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes (2015)
Journal Article
Burroughs, L., Eccleshare, L., Ritchie, J., Kulkarni, O., Lygo, B., Woodward, S., & Lewis, W. (2015). One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes. Angewandte Chemie International Edition, 54(36), https://doi.org/10.1002/anie.201505347

An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of orthofused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives coul... Read More about One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes.

New furocarbazole alkaloids from Lonicera quinquelocularis (2015)
Journal Article
Khan, D., Khan, S., Badshah, S., Ullah, H., Ullah, H., Muhammad, Z., & Woodward, S. (2016). New furocarbazole alkaloids from Lonicera quinquelocularis. Natural Product Research, 30(1), https://doi.org/10.1080/14786419.2015.1036267

Two new furocarbazole alkaloids, 3-formyl-6,7-dimethoxy-furo[1,2]carbazole (1) and methyl-6,7-dimethoxy-furo[1,2]carbazole-3-carboxylate (2), along with two known carbazole alkaloids, 3-formyl-2-hydroxy-7-methoxycarbazole (3) and methyl 2,7-dimethoxy... Read More about New furocarbazole alkaloids from Lonicera quinquelocularis.

Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene (2015)
Journal Article
Burroughs, L., Ritchie, J., Ngwenya, M., Khan, D., Lewis, W., & Woodward, S. (2015). Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene. Beilstein Journal of Organic Chemistry, 11, https://doi.org/10.3762/bjoc.11.31

1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C6H4(CHO)2 undergo cascades to tetracenes on simple admixture of LiHDMS, CS2 and MeI. Acene formation proceeds by [3,3]-sigmatropic rearrangement... Read More about Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene.