1996
DOI: 10.1107/s0108270196002740
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3-tert-Butyl-4-methyl-2-phenyl-3-(trimethylsilyloxy)oxetane and 2-(2-Benzyloxyphenyl)-3-tert-butyl-3-(trimethylsilyloxy)oxetane

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Cited by 4 publications
(4 citation statements)
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“…However, in practice this usefulness is often tempered by an unfortunate proclivity to facile air oxidation at ambient temperatures which leads to peroxide formation. The structures of the few related compounds viz., 4-(benzyloxy)-2-fluorobenzonitrile (Yan et al, 2007), 2-benzyloxy-3-nitropyridine (Cui et al, 2005), 2,6-bis[2-(4-benzyloxyphenyl)ethyl]biphenyl (Moratti et al, 2007), 3-tert-butyl-4-methyl-2-phenyl-3-(trimethylsilyloxy)oxetane and 2-(2-benzyloxyphenyl)-3-tert-butyl-3-(trimethylsilyloxy)oxetane (Kotila et al, 1996), bislactim ethers of cyclic dipeptides: Compounds derived from cyclo(Gly-L-Val) (Bolte et al, 1999) and 5-benzyloxy-1phenyltetrazole: catalytic transfer hydrogenolysis of benzyl ethers (Brigas et al, 1999) are already reported. In view of the importance of ethers, the synthesis and crystal structure of the title compound, (I), is reported.…”
Section: Methodsmentioning
confidence: 99%
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“…However, in practice this usefulness is often tempered by an unfortunate proclivity to facile air oxidation at ambient temperatures which leads to peroxide formation. The structures of the few related compounds viz., 4-(benzyloxy)-2-fluorobenzonitrile (Yan et al, 2007), 2-benzyloxy-3-nitropyridine (Cui et al, 2005), 2,6-bis[2-(4-benzyloxyphenyl)ethyl]biphenyl (Moratti et al, 2007), 3-tert-butyl-4-methyl-2-phenyl-3-(trimethylsilyloxy)oxetane and 2-(2-benzyloxyphenyl)-3-tert-butyl-3-(trimethylsilyloxy)oxetane (Kotila et al, 1996), bislactim ethers of cyclic dipeptides: Compounds derived from cyclo(Gly-L-Val) (Bolte et al, 1999) and 5-benzyloxy-1phenyltetrazole: catalytic transfer hydrogenolysis of benzyl ethers (Brigas et al, 1999) are already reported. In view of the importance of ethers, the synthesis and crystal structure of the title compound, (I), is reported.…”
Section: Methodsmentioning
confidence: 99%
“…For related structures, see: Yan et al (2007); Cui et al (2005); Moratti et al (2007); Kotila et al (1996). For compounds related to bis-lactim ethers of cyclic dipeptides, see: Bolte et al (1999).…”
Section: Related Literaturementioning
confidence: 99%
“…The major product was an α-hydroxyketone (47% yield), which was tentatively assigned the depicted configuration 13 based on the assumption that an inversion at the former C-2 carbon atom of oxetane 12 has occurred. The structure of compound 12 in the crystal shows an anticlinal arrangement of the C-2/O and the t -Bu/C-3 bond (dihedral angle = 122.9°) which should facilitate a backside attack of the migrating group, as was postulated for the analogous migration 7 → 9 .…”
mentioning
confidence: 86%
“…Indeed, there is precedence cleaved during the rearrangement. [12] The anisyl substituent for the ring-opening of oxetes by this pathway. [20] The in compound 16, however, stabilizes a free carbenium ion torque selectivity of the ring opening, which favours the and the better migrating ability of the hydroxymethyl group outward rotation of the phenyl substituent, [21] [22] is responis the decisive factor that leads to formation of compound sible for the exclusive formation of the (E)-double bond in 17.…”
mentioning
confidence: 99%