Lithium tributylstannane

C(6) position of the pyrone nucleus [126]. Interestingly, allenylstannane. readily prepared from propargyl tosylate by copper-mediated addition of lithium tributylstannane, was coupled with 2-iodothiophene to provide a rapid entry to 2-thienylallene (187) [127],... 

Addition reactions of various a-alkoxy lithium and a-alkoxy magnesium compounds 13, formed via the corresponding tributylstannanes, have been performed8. In every case the... 

In order to establish the correct absolute stereochemistry in cyclopentanoid 123 (Scheme 10.11), a chirality transfer strategy was employed with aldehyde 117, obtained from (S)-(-)-limonene (Scheme 10.11). A modified procedure for the conversion of (S)-(-)-limonene to cyclopentene 117 (58 % from limonene) was used [58], and aldehyde 117 was reduced with diisobutylaluminium hydride (DIBAL) (quant.) and alkylated to provide tributylstannane ether 118. This compound underwent a Still-Wittig rearrangement upon treatment with n-butyl lithium (n-BuLi) to yield 119 (75 %, two steps) [59]. The extent to which the chirality transfer was successful was deemed quantitative on the basis of conversion of alcohol 119 to its (+)-(9-methyI mande I ic acid ester and subsequent analysis of optical purity. The ozonolysis (70 %) of 119, protection of the free alcohol as the silyl ether (85 %), and reduction of the ketone with DIBAL (quant.) gave alcohol 120. Elimination of the alcohol in 120 with phosphorus oxychloride-pyridine... 

Lithium tetrahydroaluminate Lithium tetrahydridoaluminate Sodium tetrahydroborate Sodium tetrahydridoborate Lithium trialkoxyhydridoaluminate Sodium bis(2-methoxyethoxy)dihydro-aluminate Diisobutylalane Tributylstannane... 

Geminal dihalides undergo partial or total reduction. The latter can be achieved by catalytic hydrogenation over platinum oxide [512], palladium [512] or Raney nickel [63, 512], Both partial and total reduction can be accomplished with lithium aluminum hydride [513], with sodium bis(2-meth-oxyethoxy)aluminum hydride [514], with tributylstannane [503, 514], electro-lytically [515], with sodium in alcohol [516] and with chromous sulfate [193, 197]. For partial reduction only, sodium arsenite [220] or sodium sulfite [254] are used. 

Chemical reduction of aromatic aldehydes to alcohols was accomplished with lithium aluminum hydride [5i], alane [770], lithium borohydride [750], sodium borohydride [757], sodium trimethoxyborohydride [99], tetrabutylam-monium borohydride [777], tetrabutylammonium cyanoborohydride [757], B-3-pinanyl-9-borabicyclo[3.3.1]nonane [709], tributylstannane [756], diphenylstan-nane [114], sodium dithionite [262], isopropyl alcohol [755], formaldehyde (crossed Cannizzaro reaction) [i7i] and others. 

Other methods, among which thermolysis or photolysis of tetrazene [59], photolysis of nitrosoamines in acidic solution [60], photolysis of nitrosoamides in neutral medium [61], anodic oxidation of lithium amides [62], tributylstannane-mediated homolysis of O-benzoyl hydroxamic derivatives [63, 64], and spontaneous homolysis of a transient hydroxamic acid sulfinate ester [65] could have specific advantages. The redox reaction of hydroxylamine with titanium trichloride in aqueous acidic solution results in the formation of the simplest protonated aminyl radical [66] similarly, oxaziridines react with various metals, notably iron and copper, to generate a nitrogen-centered radical/oxygen-centered anion pair [67, 68]. The development of thiocarbazone derivatives by Zard [5, 69] has provided complementary useful method able to sustain, under favorable conditions, a chain reaction where stannyl radicals act simply as initiators and allow transfer of a sulfur-containing... 

A Vnsh coupling of 24 Hz has been observed by Santiago et in the spectrum of trans-4-terf-butyl-2-(tributylstannane)piperidine but not in that of its cis isomer. In the first case the lone nitrogen pair and the C-Sn bond are eclipsed, in the other antiplanar. The authors also noticed that the tin-lithium transmetallation proceeds very easily for the trans compound, whereas isomer cis does not undergo this process. 

The synthesis of the TT 36, possessing a 3-mercaptoprop-l-yl tmit at C-2 was achieved through the reaction of aldehyde 6 with lithium-2-trimethylsilyl-l,3-dithian-2-ide (34) and tributylstannane successively (Scheme 7) [26]. 

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