Thioaldehyde Diels-Alder reactions

Vedejs, E.; Eberlein, Thomas H.; Mazur, D. J.; McClure, Cynthia K.; Perry, David A.; Ruggeri, Roger B.; Schwartz, Eben S.; Stults, J. S.; Varie, David L.; Wilde, Richard G.; Wittenberger, Steven J.

doi:10.1021/jo00359a034

Cited by 126 publications

(32 citation statements)

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“…Therefore, the starting material was diphenacyl disulfide 18, prepared easily and in high yield through a modified literature method [22] from phenacyl mercaptan. [23] After protection of 18 as dioxolane 19 [24] in 81 % yield, acetylene 20 was obtained by reaction of 19 with lithium trimethylsilyl acetylene in THF at 0°C in 80 % yield. Compound 21 was obtained through desilylation with TBAF at 0°C, which occurred in 93 % yield (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Regiocontrolled Synthesis of Ring‐Fused Thieno[2,3‐c]pyrazoles through 1,3‐Dipolar Cycloaddition of Nitrile Imines with Sulfur‐Based Acetylenes

Chandanshive¹,

Bonini²,

Gentili³

et al. 2010

Eur J Org Chem

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Section: Resultsmentioning

confidence: 99%

Regiocontrolled Synthesis of Ring‐Fused Thieno[2,3‐c]pyrazoles through 1,3‐Dipolar Cycloaddition of Nitrile Imines with Sulfur‐Based Acetylenes

Chandanshive¹,

Bonini²,

Gentili³

et al. 2010

Eur J Org Chem

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“…Starting materials were prepared by known procedures: 1, [16] 2, [17] 3, [18] 4, [18] 5, [18] 6, [19] 7, [20] 8.…”

Section: Resultsmentioning

confidence: 99%

Reactions of Fischer Carbene Complexes with Siloxydienes: Formation of Cycloheptadiene and Cyclopentene Derivatives—Formal [2+1] Cycloaddition Followed by Cope Rearrangement Versus Formal [3+2] Cycloaddition with or without Preceding Carbene-Ligand Metathesis

Hoffmann¹,

Buchert²,

Reißig³

1999

Chem. Eur. J.

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Thermal reactions of the a,bunsaturated Fischer carbene complexes 3 ± 5 with the siloxydienes 6 and 7 mainly furnished the expected cyclohepta-1,4-dienes such as 9, 10, 12, 14, and 15, whose formation is explained by a formal [21] cycloaddition followed by Cope rearrangement. The rather electron-rich carbene complex 5 also afforded the cyclopentene derivatives 11 and 16 as by-products, which are probably formed by two distinct mechanisms. Single diastereomers of the cyclopentene derivatives 17 and 18 were isolated as the exclusive products of the reactions of 3 and 4, respectively, with the donor/ acceptor-substituted 1,3-diene 8. This process is interpreted as a metalla Diels ± Alder reaction to form a chromacyclohexene intermediate 25, which subsequently undergoes fragmentation to give cyclopentene derivatives with the required constitution. Most surprisingly, the reactions of simple carbene complexes 1 or 2 with the siloxydienes 7 or 8 yielded cyclopentene derivatives 19 and 20 that do not contain the carbene ligand of the precursor complexes. Instead, the constitution of the isolated products can be accounted for by a formal diene dimerization with fragmentation of a methylene unit. Their formation can be interpreted by an unprecedented sequence of carbene-ligand metathesis followed by a metalla Diels ± Alder reaction and reductive fragmentation. All these results illustrate the great importance of electronic fine-tuning in the precursors involved in reactions of Fischer carbene complexes with 1,3-dienes.

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“…Some of these complexes were previously identified in our earlier screening study [5]. Although metal complexes of the thiolate ligands PhNHC(O)CH 2 S À [15,16] and MeO 2 CCH 2 S À [17][18][19] are well known, and the thiols PhC(O)CH 2 SH [20] and EtO 2 CCH 2 C(O)CH 2 SH [21] are reported, the other thiolate ligands (or the free thiols) contained in complexes 3e-3o appear to be new ligands.…”

Section: Syntheses and Spectroscopic Characterisationmentioning

confidence: 90%

Dinuclear platinum complexes with designer thiolate ligands from the monoalkylation of [Pt2(μ-S)2(PPh3)4]

Ujam

Devoy

Henderson

et al. 2010

Inorganica Chimica Acta

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a b s t r a c tAlkylation reactions of the nucleophilic platinum(II) sulfide complex [Pt 2 (l-S) 2 (PPh 3 ) 4 ] with functionalised alkylating agents have been investigated as a versatile synthetic route to dinuclear, cationic sulfidethiolate complexes of the type [Pt 2 (l-S)(l-SR)(PPh 3 ) 4 ] + , extending the range of thiolate complexes that can be prepared using this methodology. A wide range of functional groups can be incorporated, using appropriate alkylating agents, and include ketone, ester, amide, hydrazone, semicarbazone, thiosemicarbazone, oxime, guanidine, urea and thiourea groups.

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Thioaldehyde Diels-Alder reactions

Cited by 126 publications

References 0 publications

Regiocontrolled Synthesis of Ring‐Fused Thieno[2,3‐c]pyrazoles through 1,3‐Dipolar Cycloaddition of Nitrile Imines with Sulfur‐Based Acetylenes

Regiocontrolled Synthesis of Ring‐Fused Thieno[2,3‐c]pyrazoles through 1,3‐Dipolar Cycloaddition of Nitrile Imines with Sulfur‐Based Acetylenes

Reactions of Fischer Carbene Complexes with Siloxydienes: Formation of Cycloheptadiene and Cyclopentene Derivatives—Formal [2+1] Cycloaddition Followed by Cope Rearrangement Versus Formal [3+2] Cycloaddition with or without Preceding Carbene-Ligand Metathesis

Dinuclear platinum complexes with designer thiolate ligands from the monoalkylation of [Pt2(μ-S)2(PPh3)4]

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