1973
DOI: 10.1055/s-1973-22137
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The Synthesis of [2.2]Phanes

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Cited by 110 publications
(42 citation statements)
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“…For instance, by adding a tenfold excess of lithium powder to a solution of 3 in dry THF at 0 °C we obtained only compound 4, in 25% isolated yield, along with some intractable material (Scheme 2). 16 Si(i-Pr) 3 Si(i-Pr) 3 (i-Pr) 3 …”
Section: Methodsmentioning
confidence: 99%
“…For instance, by adding a tenfold excess of lithium powder to a solution of 3 in dry THF at 0 °C we obtained only compound 4, in 25% isolated yield, along with some intractable material (Scheme 2). 16 Si(i-Pr) 3 Si(i-Pr) 3 (i-Pr) 3 …”
Section: Methodsmentioning
confidence: 99%
“…[28][29][30][31][32][33] On the other hand, aromatic hydrogens of anti-4a appear at slightly low field than that of syn-4b and syn-4c. The tert-butyl protons were also observed higher field at δ 1.03, 1.12 ppm for compound 4b and δ 1.08 ppm for compound 4c, compared to that of analogue anti-5a and anti-5b at δ 1.27 and 1.36 ppm due to the strong shielding effect of the benzene ring.…”
Section: Resultsmentioning
confidence: 99%
“…2, bottom), it seen that the two benzene ring are closest face to face and due to ring current the aromatic protons are shielded to high field at δ 1.08 ppm ( ppm for the protons of the aromatic rings due to shielded by the adjacent ring, a common consequence of a face-to-face benzene ring. [28][29][30][31][32][33] The tert-butyl protons for compounds syn-6b were observed at higher field at δ 1.10 and 1.14 ppm compared to those of the anti-7b at δ 1.22 and 1.27 ppm due to the shielding effect of the benzene ring. These observations strongly suggest that compound 6b adopts syn-conformation.…”
Section: Resultsmentioning
confidence: 99%
“…The 1 H NMR spectrum (in CDCl 3 ) of anti-4d exhibits two sets of doublets at = 3.28, 3.76 ppm (J = 15.0 Hz) and = 3.40, 3.45 ppm (J = 13.2 Hz) for the ArCH 2 COCH 2 Ar methylene protons and a singlet for the internal methoxy group at an = 3.36 ppm from anisole ( = 3.75 ppm) due to the ring current of the opposing aromatic ring. [26][27][28][33][34][35][36][37][38] Similarly, the internal aromatic proton at 18-position was 5.39 ppm compared to that of the 3b at 7.28 ppm. These observations strongly suggest that compound anti-4d adopts the anti-conformation.…”
Section: Resultsmentioning
confidence: 99%