1. Yields of the ester 30a (3.61 mg, 0.0134 mmol, 33%) and phenanthrene (6.80 mg, 0.0382 mmol, 94%) were thus determined. Bii. Photolysis of 18 in benzylamine: Precursor 18 (150 mg, 0.441 mmol) and benzylamine (92.1 �L, 90.4 mg, 0.845 mmol) were dissolved in benzene (4.5 mL) in a quartz pressure tube. Photolysis was monitored by GC-MS and TLC until all 18 had reacted, or 6 hrs. The amide (30b) was isolated using silica-gel flash column chromatography (0:100 ? 50:50 ethyl acetate:hexanes) in a 31% yield. Biii. Photolysis of 18 in benzylamine and m-xylene: Precursor 18 (13.0 mg, 0.0384 mmol) was dissolved in C 6 D 6 (0.5 mL) in a quartz NMR tube;Photolysis was monitored by NMR until all 18 had reacted
2. 85 mg, 0.0366 mmol, 95%) and phenanthrene (6.59 mg, 0.0370 mmol, 96%) were thus determined. Biv. Photolysis of 18 without an internal trap: Precursor 18 (30.0 mg, 0.0881 mmol) was dissolved in benzene (2 mL) in a long-necked quartz cuvette. The solution was photolyzed for 7 hrs, checking via GC-MS once every hour. Ketene 13 was observed, along with a minor amount of 2-adamantanone and trace amounts of 2-adamantylcarboxylic acid. The addition of benzylamine (1 mL) to the photolysate and immediate analysis with GC-MS showed full References (1) Roth;Org. Biomol. Chem,2023