1975
DOI: 10.1021/jo00892a015
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Conformational analysis of 1,3-dioxacyclohept-5-enes. Proton and carbon-13 magnetic resonance. Evidence for a twist-boat conformation

Abstract: Twist-boat conformations have been assigned to cisand trans-4,7-dimethyl-1,3-dioxacyclohept-5-ene and to r-2-tert-butyl-cis-4,irons-7-dimethyl-l,3-dioxacyclohept-5-ene on the basis of carbon-13 substituent effects. These assignments are consistent with pmr spectra. The data also suggest that 2,2-dimethyl-l,3-dioxacyclohept-5-ene is in a twist-boat conformation but r-2-tert-butyl-cis-4,c:s-7-dimethyl-l,3-dioxacyclohept-5-ene is in a chair conformation.Conformational analysis of the 1,3-dioxacycloalkanes has rec… Show more

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Cited by 23 publications
(7 citation statements)
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“…and 54% respectively. The 'H nmr spectra of each compound were found to be identical to those reported earlier for l b (9, 21), 36 (21), and 5b (9). The 13C nmr chemical shifts reported in Table 1 confirm the identity of each compound.…”
Section: The Conformational Effect Of the Benzo Groupsupporting
confidence: 79%
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“…and 54% respectively. The 'H nmr spectra of each compound were found to be identical to those reported earlier for l b (9, 21), 36 (21), and 5b (9). The 13C nmr chemical shifts reported in Table 1 confirm the identity of each compound.…”
Section: The Conformational Effect Of the Benzo Groupsupporting
confidence: 79%
“…The 'H nmr spectrum was found to be identical to that published (9,21) while the 13C nmr data reported in Table 1 confirm the structure.…”
Section: 2-supporting
confidence: 71%
See 1 more Smart Citation
“…2-Methoxy-l,3-dioxa-5,6-benzocycloheptene (10). A mixture of 3.0 g (0.0217 mol) of 1,2-benzenedimethanoI, 2.4 mL (0.0219 mol) of trimethyl orthoformate, 3 mL of benzene, and 20 mg of p-toluenesulfonic acid was stirred for 2 h at room temperature.…”
Section: -Methyl-13-dioxa-56-benzocycloheptenementioning
confidence: 99%
“…This isomerization process is most likely catalyzed by a ruthenium hydride species generated by catalyst decomposition. 46 Because of the twist boat conformation of dioxepins, 47 intramolecular aryl-vinyl π-stacking interactions in 3b 48 sterically hinder olefin isomerization. We were concerned that the copolymer microstructure would be irregular should the isomerization products participate in AROMP.…”
Section: ■ Introductionmentioning
confidence: 99%