Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

• Filipe Vilela,
• Peter J. Skabara,
• Christopher R. Mason,
• Thomas D. J. Westgate,
• Asun Luquin,
• Simon J. Coles and
• Michael B. Hursthouse

Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113

• derivatives have been reported [19], treatment of 22 with triethyl phosphite did not give the desired self-coupled TTF compound 23. The X-ray structure of 22 is shown in Figure 3. The molecule possesses an inversion centre located at the C(22)–C(22’) bond. A close intramolecular contact is observed between S

• processability for the annelated products [23][24][25]. The thione group in 3 has the potential for several synthetically useful manipulations (Scheme 6). Compound 3 was shown to be a synthetically versatile compound. Refluxing of 3 in triethyl phosphite followed by purification by filtration through silica gel

• ) and 3.69 (4H, s); νmax (KBr)/cm−1 2935, 1612 and 1059. 2,2’-Bis[(8-(2-thienyl)thieno[2,3-f][1,3]benzodithiolylidene)] (25) 8-(2-Thienyl)thieno[2,3-f][1,3]benzodithiole-2-thione 3 (0.377 g, 1.17 mmol) was suspended in the minimal amount of freshly distilled triethyl phosphite (<5 ml) under a nitrogen

Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl- 5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro- 2H-quinolizin- 1-yl]methanol

• Joseph P. Michael,
• Claudia Accone,
• Charles B. de Koning and
• Christiaan W. van der Westhuyzen

Beilstein J. Org. Chem. 2008, 4, No. 5, doi:10.1186/1860-5397-4-5

• was then effected by first treating the thiolactam with ethyl bromoacetate, after which reaction of the resulting S-alkylated intermediate with triethyl phosphite and triethylamine in acetonitrile gave the vinylogous urethane (+)-28 in 75% yield. At this stage, however, our fears of the discrepant

New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline- 2,4(1H,3H)-dione compounds

• Oldřich Paleta,
• Karel Pomeisl,
• Stanislav Kafka,
• Antonín Klásek and
• Vladislav Kubelka

Beilstein J. Org. Chem. 2005, 1, No. 17, doi:10.1186/1860-5397-1-17

• 72 Zlín, Czech Republic Zentiva, U Kabelovny 130, 10237 Prague 10, Czech Republic 10.1186/1860-5397-1-17 Abstract Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives react with triethyl phosphite to afford either the product of the Perkow reaction or

• the sugar skeleton and its multiple acetoxy groups. In this communication we would like to report on the ability of halocarboxylate anions to act as leaving groups in the reactions of 3-(haloacyloxy)-quinoline-2,4(1H,3H)-diones with triethyl phosphite to afford 8 and 9, the products of the Perkow

• -3-(fluoroiodoacetoxy)quinoline-2,4(1H,3H)-dione (4) was reacted with triethyl phosphite an unexpected product 9 (Scheme 3) was obtained instead of the desired Horner-Wadsworth-Emmons intermediate 1-benzyl-3-butyl-3-(diethoxyphosphoryl)fluoroacetyloxy-quinoline-2,4(1H,3H)-dione. We assume the newly