2009
DOI: 10.1002/ejoc.200801101
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2‐Hydroxybenzocyclobutenone Ethylene Dithioacetals as Precursors of Highly Substituted 1,4‐Dihydronaphthalenes

Abstract: Abstract1,4‐Dihydronaphthalenes 2, 9, and 11 with a spiro‐connected 1,3‐dithiolane ring as well as tetrahydronaphthalenes 15, 17, and 19 have been obtained from o‐quinodimethanes 3 and alkynes 4, naphthoquinones 10, or alkenes 14 and 16. Benzocyclobutenol 6 is not an appropriate quinodimethane precursor as it readily rearranges to phthalaldehyde derivative 7. However, silyl ether 8, silyl ether 13, obtained by the hydrosilylation of cyclobutenol 5, or aluminium alkoxide 3d, generated in situ by DIBAL reduction… Show more

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Cited by 21 publications
(9 citation statements)
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“…The IR spectra of these adducts lack the presence of a carbonyl absorption but do show the presence of an imino absorption at approximately 1690 cm À1 . Similarly, their 13 C NMR spectra show no carbonyl resonance, but they do show the absorption for the imino carbon at approximately d 165. Chemical evidence for their assigned structures rests on their observed acid-catalyzed hydrolysis to give the vinylogous hemiacetal 28 (Scheme 12).…”
Section: Synthesis Of 4-iminocyclobutenonesmentioning
confidence: 97%
See 1 more Smart Citation
“…The IR spectra of these adducts lack the presence of a carbonyl absorption but do show the presence of an imino absorption at approximately 1690 cm À1 . Similarly, their 13 C NMR spectra show no carbonyl resonance, but they do show the absorption for the imino carbon at approximately d 165. Chemical evidence for their assigned structures rests on their observed acid-catalyzed hydrolysis to give the vinylogous hemiacetal 28 (Scheme 12).…”
Section: Synthesis Of 4-iminocyclobutenonesmentioning
confidence: 97%
“…Selected examples include monothionation of semisquaric 3 to give the corresponding 4-thioxocyclobut-2-enones. [11] Also 1,3-dithiolane derivatives of cyclobutenones have been synthesized, [12,13] which can be considered as protected cyclobutenethiones. [14][15][16] There are also scattered examples of cyclobutenimine derivatives in the literature.…”
Section: Introductionmentioning
confidence: 99%
“…80 Cyclobutenol 162, prepared by reduction of benzocyclobutenedione monothioketal, smoothly rearranged to aldehyde 163 at r.t. via ring opening and subsequent 1,5-hydrogen shift (Scheme 68). 81 However, the corresponding silyl ether was stable enough to be stored at r.t. The silyl ether 164 existed in equlibrium with the corresponding ring-opened product 165 (Scheme 69).…”
Section: [4 þ 2] Cycloaddition Of O-quinodimethanesmentioning
confidence: 99%
“…Protection of carbonyl groups as thioacetals is quite often a necessary requirement in the synthesis of multiple functional organic molecules [1,2]. This is because of their stability both in acidic and basic conditions.…”
Section: Introductionmentioning
confidence: 99%