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1 Supporting Information Calix[4, 5]tetrolarenes: A New Family of Macrocycles Yossi Zafrani* and Yoram Cohen* School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv 69978, Tel Aviv, Israel. The Department of Organic Chemistry, Israel Institute for Biological Research, Ness-Ziona 74000, Israel. Table of Contents 1. Materials and Methods S2 2. Experimental procedures and characterization of compounds 4a, 5a and 5b S H and 13 C NMR spectra of 4a, 5a and 5b S5 4. HSQC analysis of 5a S8 5. X-ray data of 4a and 5a S9 S1
2 1. Materials and Methods. Starting materials were purchased from Sigma-Aldrich and Alfa Aesar and were used without further purification. Chemical reactions were monitored by TLC (Merck, silica gel 60 F254) and the compounds were purified by SiO 2 flash chromatography (Merck Kieselgel 60). NMR spectra were obtained on 11.7T or on 9.4T Bruker NMR spectrometers. Chemical shifts (δ) are given in part per million (ppm) and spin-spin coupling (J) in Hz. The chemical shifts are quoted relative to residual CHCl 3 signal (at δ 7.26 ppm for the 1 H NMR and 77.2 ppm for the 13 C NMR) when the solvent was CDCl 3. Line shape abbreviations are as follows: singlet (s), broad singlet (bs), doublet (d), AB-quartet (AB-q), multiplet (m). The barrier for ring inversion was calculated using a total line-shape analysis by gnmr. High-resolution electrospray mass spectra were recorded on a Waters Synapt instrument. X-ray diffraction were performed on an ApexDuo (Bruker- AXS) diffractometer system using MoKα (λ = A) radiation. The measurements were performed at -163 C. For 4a, a total of 497 frames were collected and the total exposure time was 1.38 hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a monoclinic unit cell yielded a total of reflections to a maximum θ angle of (0.75 Å resolution), of which 8859 were independent (average redundancy 4.220, completeness = 99.6%, R int = 3.85%, R sig = 4.01%) and 6377 (71.98%) were greater than 2σ(F 2 ). For 5a, a total of 424 frames were collected and the total exposure time was 2.36 hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a triclinic unit cell yielded a total of reflections to a maximum θ angle of (0.84 Å resolution), of which 8302 were independent (average redundancy 2.285, completeness = 98.6%, R int = 5.03%, R sig = 8.51%) and 5242 (63.14%) were greater than 2σ(F 2 ). S2
3 2. Experimental procedures and characterization Synthesis of 4a and 5a: Syntheses were performed based on previously described procedure with some modifications. 1 To a solution of 3a (5 mmol, 0.92 g) in dichloroethane (DCE) (40 ml), paraformaldehyde (5 mmol, 0.15 g) and trifluoroacetic acid (TFA, 2.5 ml) were added. The reaction mixture was heated to 70 o C for 2 h and the color became orange. The solvent was removed under reduced pressure before the crude mixture was solubilized in chloroform and excess of sodium carbonate was added. The mixture was stirred for few minutes and filtered off and then solvent was removed under reduced pressure. The products were separated by column chromatography using a gradient of 0-30 % ethyl acetate-hexane as eluent. 4a and 5a were obtained in 53 % and 20 % isolated yields (0.528 g and 0.2 g), respectively. Both isolated products were crystallized by slow diffusion of acetonitrile to the chloroform solutions of 4a and 5a. 4a. 1 H-NMR (400 MHz, CDCl 3 ): δ (ppm) 8.90 (s, 4OH), 3.88 (bs, 4CH 2 ), 3.76 (s, 4OCH 3 ), 3.74 (s, 8OCH 3 ). 13 C-NMR (100 MHz, CDCl 3 ): δ (ppm) 151.1, 147.4, 140.8, 115.9, 60.8, 60.6, HRMS: m/z calcd. for C 40 H 47 O 16 [M-H] , found a. 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 7.90 (bs, 5OH), 3.82 (s, 5CH 2 and 15OCH 3 ). 13 C NMR (100 MHz, CDCl 3 ): δ (ppm) 150.5, 148.1, 140.4, 115.9, 61.0, 60.7, HRMS: m/z calcd. for C 50 H 59 O 20 [M-H] , found Synthesis of 5b (in a mixture with its related hexamers, heptamer, octamer and nonamer). To a solution of 3b (5 mmol, g) in dichloroethane (40 ml), paraformaldehyde (5 mmol, 0.15 g) and trifluoroacetic acid (TFA, 2.5 ml) were added. The reaction mixture was stirred at room temperature for 72 h and the color became orange. The solvent was removed under reduced pressure and then the crude mixture was solubilized in chloroform with excess of sodium carbonate. The mixture was stirred for few minutes and filtered off before the solvent was removed under reduced pressure. The mixture of the cyclic products was slowly S3
4 precipitated by the addition of methanol to a concentrated solution of the crude in dichloromethane in a total isolated yield of 57%. The pentameric product 5b (ca 40 %) and its hexameric, heptameric, octameric and nonameric derivatives were identified by LC-MS analysis. Both 1 H and 13 C NMR spectra of these products were found to be almost identical. 5b: 1 H NMR (500 MHz, CDCl 3 ): δ (ppm) 3.98 (s, 5CH 2 ), 3.73 (s, 5OCH 3 ), 3.55 (s, 5OCH 3 ), 3.44 (s, 10OCH 3 ). 13 C NMR (125 MHz, CDCl 3 ): δ (ppm) 152.9, 150.5, 143.2, 124.1, 60.7, 60.2, 60.1, 20.1 HRMS: m/z calcd. for C 55 H 70 O 20 [M- Na] , found S4
5 OMe MeO OMe OH 4 OH Figure S1. NMR spectra of 4a in CDCl 3 at room temperature; (top) 500 MHz 1 H NMR spectrum and (bottom) 125 MHz 13 C NMR spectrum. S5
6 OH Figure S2. NMR spectra of 5a in CDCl 3 at room temperature; (top) 500 MHz 1 H NMR spectrum and (bottom) 125 MHz 13 C NMR spectrum. S6
7 Figure S3. NMR spectra of 5b (as a major product in a mixture of hexamer, heptamer, octamer and nonamer) in CDCl 3 at room temperature; (top) 500 MHz 1 H NMR spectrum and (bottom) 125 MHz 13 C NMR spectrum. S7
8 10 OCH 3, 5 OCH 3, 5 CH 2 5 CH OCH 3 Figure S4: HSQC 2D NMR spectra of 5a in CDCl 3 S8
9 Table S1: Sample and crystal data for 4a. Table S2: Data collection and structure refinement for 4a. S9
10 Table S3: Sample and crystal data for 5a. Table S4: Data collection and structure refinement for 5a. S10
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