Triton B

Triton B Trade name for benzyltrimethyl-ammonium hydroxide usually as a 40% solution in methanol. A strong base, soluble in many solvents used as a catalyst. See phase transfer chemistry. 

Tos, Ts [(4-methylphenyl)sulfonyl3 = p-tolueoesulfbnyl), tosyl Triton B benzyltrimeihylammonium hydroxide = Blma OH", PhCHjNMej OH-... 

Tritium peroxide Tritonals Triton B Triton N Triton RW... 

Benzyltrimethylammonium hydroxide (Triton B) [100-85-6] M 167.3, d 0.91. A 38% soln (as supplied) was decolorized (charcoal), then evaporated under reduced pressure to a syrup, with final drying at 75° and 1 mm pressure. Prepared anhydrous by prolonged drying over P2O5 in a vacuum desiccator. 

Alkylation at the ind-N of l,2,3,4-tetrahydro-j8-carbolines has been carried out with alkyl halide after treatment with sodamide in the usual manner. Cyanoethylation of a p /r-V-substituted tetrahydro-jS-carboline in the presence of Triton B yields the corresponding 9-cyanoethyl derivative. Similarly, treatment of p / -V-methyl-l,2,3,4,4a,9b-hexahydro-y-carboline with sodamide, followed by benzyl chloride, leads to the ind-A -benzyl-substituted derivatives. l-Oxo-l,2,3,4-tetrahydro-j8-carboline yields the ind-A -methyl derivative directly with dimethyl sulfate.Prolonged treatment with sodium hydride, followed by methyl iodide, yields the 2,9-dimethyl derivative. Heating with sodium hydride in acetone followed by the addition of dimethyl sulfate gives rise to the ind-V-methyl derivative. ... 

A five-step synthesis of ethyl ester of eyelie hydrazonie aeid 314 used in the synthesis of natural produets has been deseribed [94JCA(CC)1867]. The eonden-sation of methoxybutenone with EtCOaCN (t-BuOK, THF, —78°C) is eompleted with the formation of ketoester 310 in 72% yield. The addition of methanol to the latter (Triton B, MeOH, room temperature, 88%) and the reduetion with NaBH4 (EtOH, —78°C) leads to the aleohol 312, yield 90%. The dianion of 312 (EDA, THE, -78°C) reaets with t-butylazodiearboxylate (t-BuOaC—N=N—COaBu-t) to form adduet 313, the treatment of whieh with trifluoroaeetie aeid affords the ester 314 in 55% yield [94JCA(CC)1867]. 

A solution of benzyltrimethylammonium hydroxide (Triton B, 10ml, 40% in MeOH) was treated with aqueous HF (ca. 8.6ml, 4.7%) until the pH reached 8-7. The solvent was removed in vacuo (ca. 1 mm), and the residue was dried at 50°C/0.5 mmHgfor 20 h. The resulting highly hygroscopic solid was powdered, and then stored in a desiccator over P205. 

Epoxyeyclohexanone has been prepared in 30% yield4 by epoxi-dation of 2-cyclohexen-l-one with alkaline hydrogen peroxide, using a procedure described for isophorone oxide (4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one).5 A better yield (66%) was obtained using f r/-butyl hydroperoxide (1,1-dimethylethylhydroperoxide) and Triton B in benzene solution.6 The procedure described here is simple and rapid. 

The Knoevenagel condensation of a-lithiosulphoxides with hemiacetal 437 has been used to synthesize PGI2 analogues 438 (equation 261). The Knoevenagel-type condensation of dithioacetal monoxides with substituted benzaldehydes has been performed using Triton B as a base and gave the corresponding ketene dithioacetal monoxides 4395 2,513 (equation 262). 

Scheme 89. Synthesis of cis-alpinigenine (445) by photooxygenation. Reagents a, 02, Triton B, py b, hv, 02, Rose Bengal c, NaBH4 d, HC1 e, DIBAL.

Treatment of 71a with phosphorus oxychloride readily afforded the dichloro derivative 79 in 95% yield. Michael addition with methyl acrylate in the presence of Triton B led to the regioselective formation of 80 (Scheme 3)... 

The PMHS/TBAF system provides both an excellent and practical approach to the reduction of aryl ketones to the benzyl alcohols.278 Similarly, the PMHS/ Triton B combination gives high yields of the benzyl alcohols.278... 

Other systems that are highly stereoselective in the reduction of 2-substituted ketones include PMHS/Triton -B (erythro threo = 95 5),278 (TMSO SiH/ Triton -B (crythro threo = 95 5),278 and PhMe2SiH/TASF/HMPA (erythro threo = 93 7).320... 

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