1980
DOI: 10.1021/ja00533a018
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Regio- and stereoselective 1,2 Wagner-Meerwein shifts during trifluoroacetic acid catalyzed isomerization of unsymmetrically substituted tricyclo[3.2.0.02,4]heptanes

Abstract: Die Faktoren, die die Regio‐ und Stereoselektivität bei der TFA‐katalysierten Isomerisierung der Tricycloheptane (VI) bestimmen, und der Mechanismus der Reaktion werden ausführlich untersucht und diskutiert.

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Cited by 18 publications
(2 citation statements)
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“…The following supporting information can be downloaded at: https: //www.mdpi.com/article/10.3390/molecules28196764/s1, Preparation and characterization of substrates, Copies of HRMS, 1 H NMR, and 13 C NMR spectra for substrates 1b, 1d, 1k, 1m and products 3aa, 3ab, 3ac, 3ad, 3ae, 3af, 3ba, 3ca, 3df, 3ea, 3fa, 3gf, 3gf , 3ha, 3ia, 3ja, 3ka, 3la, 3ma, 3nc. References [33][34][35][36][37][38][39][40][41] are cited in Supplementary Materials.…”
Section: Supplementary Materialsmentioning
confidence: 99%
“…The following supporting information can be downloaded at: https: //www.mdpi.com/article/10.3390/molecules28196764/s1, Preparation and characterization of substrates, Copies of HRMS, 1 H NMR, and 13 C NMR spectra for substrates 1b, 1d, 1k, 1m and products 3aa, 3ab, 3ac, 3ad, 3ae, 3af, 3ba, 3ca, 3df, 3ea, 3fa, 3gf, 3gf , 3ha, 3ia, 3ja, 3ka, 3la, 3ma, 3nc. References [33][34][35][36][37][38][39][40][41] are cited in Supplementary Materials.…”
Section: Supplementary Materialsmentioning
confidence: 99%
“…H NMR (keto): δ 7.96 (d, J = 7.2 Hz, 4 H), 7.57 (t, J = 7.2 Hz, 2 H), 7.45 (t, J = 7.6 Hz, 4 H), 5.93-5.83 (m, 1 H), 5.30 (t, J = 7.2 Hz, 1 H), 5.02-5.13 (m, 2 H), 2.86-2.90 (m, 2 H). 13 C{ 1 H} NMR (keto): δ 195.9, 136.3, 135.4, 133.9, 129.2, 128.9, 117.6, 57.1, 33.9 2-Allyl-1-phenyl-1,3-butanedione (Table2, entry 3) 6. Yellow oil, 75 %.…”
mentioning
confidence: 99%