SCOPUS 정보 검색 플랫폼

Volumn , Issue 13, 2009, Pages 2068-2075

Thieme chemistry journal awardees - Where are they now? Pentafluorophenyl end-capped polyynes as supramolecular building blocks

(3) Tykwinski, Rik R a,b Kendall, Jamie b McDonald, Robert b

a UNIVERSITY OF ERLANGEN NUREMBERG (Germany)

b UNIVERSITY OF ALBERTA (Canada)

Author keywords

Alkynes; Aromatic interactions; Carbenes; Carbenoids; Crystal engineering; Polyynes; Supramolecular chemistry

Indexed keywords

1 PENTAFLUOROPHENYL 5 (TERT BUTYLDIMETHYLSILYL) 2,4 PENTADIYN 1 ONE; 1 TERT BUTYLDIMETHYLSILYL 5 DIBROMOMETHYLENE 7 PENTAFLUOROPHENYL 1,3,6, HEPTATRIYNE; 1,4 [BIS(PENTAFLUROPHENYL)] 1,3 BUTADIYNE; ALDEHYDE DERIVATIVE; DIBROMOOLEFIN; PENTAFLUOROPHENYL; PHENYLQUINONE; TRIYNE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; REWARD; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 68949171918 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217706 Document Type: Article

Times cited : (11)

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57
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- Data for 11 (C16H15F5Si, Fw, 330.37; monoclinic crystal system; space group P21/c (No. 14, a, 8.3640(5, b, 18.3726(11, c, 10.9822(7) Å; β, 104.5167(9)°; V, 1633.74(17) Å3; Z, 4; ρcalcd, 1.343 g cm-3; 2 θmax, 52.76°; μ, 0.186 mm -1; T, 80°C; total data collected, 12874; R1, 0.0381 [2844 observed reflections with Fo2 ≥ 2σ(Fo2, wR2, 0.1125 for 201 variables and 3346 unique reflections with Fo2 ≥ -3σFo2, residual electron density, 0.210 and -0.241 e Å-3. CCDC 725483
- -3. CCDC 725483.

58
- 68949185360
- Data for 27b (C23H21F5Si, Fw, 420.49; triclinic crystal system; space group P1 (No. 2, a, 7.5471(8, b, 16.2227(18, c, 18.215(2) Å; α, 83.2514(15, β, 81.0827(16, γ, 84.9478(16)°; V, 2182.3(4) Å3; Z, 4; rcalcd, 1.280 g cm-3; 2 q max, 52.00°, m, 0.155 mm-1; T, 80°C; total data collected, 14651; R1, 0.0460 [6050 observed reflections with Fo2 ≥ 2σ(Fo2, wR2, 0.1342 for 523 variables and 8490 unique reflections with Fo2 ≥ -3σFo2, residual electron density, 0.329 and -0.165 e Å-3. CCDC 725482
- -3. CCDC 725482.

59
- 68949176021
- Intermolecular distances are based on the separation of planes generated from all non-hydrogen atoms of neighboring molecules using Mercury 1.3
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60
- 68949182251
- Data for 5?decafluorotolan (4:1, C86H 20F30, Fw, 1623.02; triclinic crystal system; space group P1 (No. 2, a, 7.2628(8, b, 13.1573(14, c, 18.0306(19) Å; a, 80.3101(17, β, 82.1018(17, γ, 81.9049(18)°; V, 1670.0(3) Å3; Z, 1; ρcalcd, 1.614 g cm -3; 2θmax, 52.80°; μ, 0.152 mm -1; T, 80°C; total data collected, 13414; R 1, 0.0460 [4226 observed reflections with Fo 2 ≥ 2σ(Fo2, wR 2, 0.1494 for 523 variables and 6819 unique reflections with Fo2 ≥ -3σFo 2, residual electron density, 0.397 and -0.189 e Å-3. CCDC 725484
- -3. CCDC 725484.

61
- 68949179172
- The synthesis of 5, 10, 12, 17, and 24 has been communicated, see ref. 7.
- The synthesis of 5, 10, 12, 17, and 24 has been communicated, see ref. 7.

62
- 68949189982
- TLC analysis often indicated that reactions were complete soon after addition of base ca
- TLC analysis often indicated that reactions were complete soon after addition of base (ca. 30 min), although warming of the reaction solution in the TLC capillary could influence this analysis.
- 30 min), although warming of the reaction solution in the TLC capillary could influence this analysis

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64
- 68949176019
- General procedure for FBW rearrangements29 Unless otherwise noted in the individual procedures, in a flame-dried flask, a solution of the dibromoolefin (2.00 mmol) in anhydrous hexanes (30 mL, freshly distilled from CaH2) was cooled to -78°C under a positive pressure of N2. n-BuLi (2.5 M in hexanes, 1.05 equiv) was slowly added dropwise over a period of ca. 5 min. The reaction was allowed to warm to r.t. over ∼1 h, stirred for 3 h,30 and then quenched through the addition of aqueous NH4Cl (50 mL, Et2O (50 mL) was added, and the organic layer was separated, washed with distilled H2O (3 x 25 mL, dried over MgSO4, filtered, and the solvent removed in vacuo. Column chromatography (silica gel) gave the desired product. 3-Pentafluorophenyl-2-propynoic acid (2) Using the general procedure, 1 (0.500 g, 1.42 mmol) in hexanes (30 mL) was reacted with n-BuLi 1.15 m
- 5J = 6 Hz, 1 F), -160.3 to -160.5 (m, 2 F);

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