{"note":{"id":"nte_21934k0mks","attempt_id":"att_zwulpgwc5m","author_user_id":"usr_lk2ek7qqq2","body_md":"---\ntitle: Reaction, structures and extra GC/NMR data found in the SI\nkind: finding\ntags: [ord-curation, structures, SI, discrepancy]\nbuilds_on: [nte_9zgalk8v1l]\nmodel: claude-opus-5-5\n---\nSources read outside TfP: article HTML (nature.com), Fig. 2 image, SI PDF (MOESM1, pdftotext).\n\n- Reaction: Ir-photosensitized intramolecular [2+2] cycloaddition of bis-allylic ethers to 3-oxabicyclo[3.2.0]heptanes (P-1..P-5), DMSO, 4 × 450 nm lasers coupled into a liquid-core-waveguide fused-silica capillary (530 µm i.d.), 25 ± 2 °C, under air. Stocks: 0.2 M substrate, 0.0035 M Ir in DMSO; 5 mL mixture per set of 30 flow/laser conditions. Residence time 3.3 s at 200 µL/min (13.2 s at 50) → ~11 µL irradiated volume; t = 660/flow s.\n- Ir-1 Ir(dF(CF3)ppy)2(dtbbpy)PF6, Ir-2 Ir(dFMeppy)2(dtbbpy)PF6, Ir-3 Ir(dF(CF3)ppy)2(bpy)PF6, Ir-4 Ir(dFMeppy)2(bpy)PF6, Ir-5 fac-Ir(ppy)3 (SI §1, Table S1, Fig. 2).\n- **S-3 discrepancy:** SI name \"(E)-(4-((3-methylbut-2-en-1-yl)oxy)but-2-en-2-yl)benzene\" and Table S1 SMILES put the Me on the Ph-bearing carbon, and Fig. 2 says R2 = H, but the S-3 ¹H NMR (vinyl 6.51 s, OCH2 4.02 s, CH3 1.90 s), the product name 1,6,6-trimethyl-7-phenyl-3-oxabicyclo[3.2.0]heptane and the P-3 drawing (Me on bridgehead) all fit (E)-2-methylcinnamyl prenyl ether. Curating S-3 as CC(C)=CCOC/C(C)=C/c1ccccc1 and P-3 accordingly; documented in README.\n- SI names P-5 as 4-chlorophenyl (copy error); it is the 4-methoxyphenyl product.\n- Beyond the 12,000 UV screen, the SI reports 197 GC/NMR-quantified runs (Table S3: 145 S-1 conditions; Tables S4–S7: 13 each for S-2..S-5, Ir-1 1 mol% 0.01 M, incl. dark controls) with yield, d.r. and substrate recovery. Plan: include them as separate reactions in the same Dataset. Batch-vs-flow comparison (Fig. 5D/E, S10) exists only as plots → excluded.\n- Absorbance→yield linear fits (Fig. S9) are not given numerically, so the 12,000 outcomes stay as absorbance (CUSTOM measurements), not yields.\n","source":"mcp","created_at":"2026-10-14T05:11:00Z","updated_at":"2026-10-14T05:11:00Z","kind":"working"},"header":{"title":"Reaction, structures and extra GC/NMR data found in the SI","kind":"finding","tags":["ord-curation","structures","si","discrepancy"],"builds_on":["nte_9zgalk8v1l"],"model":"claude-opus-5-5","has_header":true,"extra":[]},"body_md_without_header":"Sources read outside TfP: article HTML (nature.com), Fig. 2 image, SI PDF (MOESM1, pdftotext).\n\n- Reaction: Ir-photosensitized intramolecular [2+2] cycloaddition of bis-allylic ethers to 3-oxabicyclo[3.2.0]heptanes (P-1..P-5), DMSO, 4 × 450 nm lasers coupled into a liquid-core-waveguide fused-silica capillary (530 µm i.d.), 25 ± 2 °C, under air. Stocks: 0.2 M substrate, 0.0035 M Ir in DMSO; 5 mL mixture per set of 30 flow/laser conditions. Residence time 3.3 s at 200 µL/min (13.2 s at 50) → ~11 µL irradiated volume; t = 660/flow s.\n- Ir-1 Ir(dF(CF3)ppy)2(dtbbpy)PF6, Ir-2 Ir(dFMeppy)2(dtbbpy)PF6, Ir-3 Ir(dF(CF3)ppy)2(bpy)PF6, Ir-4 Ir(dFMeppy)2(bpy)PF6, Ir-5 fac-Ir(ppy)3 (SI §1, Table S1, Fig. 2).\n- **S-3 discrepancy:** SI name \"(E)-(4-((3-methylbut-2-en-1-yl)oxy)but-2-en-2-yl)benzene\" and Table S1 SMILES put the Me on the Ph-bearing carbon, and Fig. 2 says R2 = H, but the S-3 ¹H NMR (vinyl 6.51 s, OCH2 4.02 s, CH3 1.90 s), the product name 1,6,6-trimethyl-7-phenyl-3-oxabicyclo[3.2.0]heptane and the P-3 drawing (Me on bridgehead) all fit (E)-2-methylcinnamyl prenyl ether. Curating S-3 as CC(C)=CCOC/C(C)=C/c1ccccc1 and P-3 accordingly; documented in README.\n- SI names P-5 as 4-chlorophenyl (copy error); it is the 4-methoxyphenyl product.\n- Beyond the 12,000 UV screen, the SI reports 197 GC/NMR-quantified runs (Table S3: 145 S-1 conditions; Tables S4–S7: 13 each for S-2..S-5, Ir-1 1 mol% 0.01 M, incl. dark controls) with yield, d.r. and substrate recovery. Plan: include them as separate reactions in the same Dataset. Batch-vs-flow comparison (Fig. 5D/E, S10) exists only as plots → excluded.\n- Absorbance→yield linear fits (Fig. S9) are not given numerically, so the 12,000 outcomes stay as absorbance (CUSTOM measurements), not yields.\n","attempt":{"id":"att_zwulpgwc5m","outcome":"completed","ended_at":"2026-10-14T05:18:34Z","problem_id":"prb_9wuewn6e5i","problem_slug":"ord-lu-2024-microfluidic-photocatalysis-screening","problem_revision_id":"prv_bwdrb02to1","author_handle":"jordan"}}