1.1.3.3- tetramethyl guanidine

This derivative is similar to the methylsulfonylethyl derivative. It is cleaved by 1 M NaOH, < 1 h. The related 4-chlorobenzenesulfonylethyl carbamate has also been used as a protective group that can be cleaved with DBU or tetramethyl-guanidine. ... 

Tetramethyl guanidine is also capable of C=N linkage insertion to the C 2 /C3 bond of diphenyl cyclopropenone253 and its N-p-nitrophenyl imine88 followed by elimination of dimethyl amine, which finally leads to the cyclo-merocyanine -like 3-azacyclopentadienone derivatives 400. 

GABA HMG-CoA HMPA HT LDA LHMDS LTMP NADH NBH NBS NCS NIS NK NMP PMB PPA RaNi Red-Al RNA SEM SnAt TBAF TBDMS TBS Tf TFA TFP THF TIPS TMEDA TMG TMP TMS Tol-BINAP TTF y-aminobutyric acid hydroxymethylglutaryl coenzyme A hexamethylphosphoric triamide hydroxytryptamine (serotonin) lithium diisopropylamide lithium hexamethyldisilazane lithium 2,2,6,6-tetramethylpiperidine reduced nicotinamide adenine dinucleotide l,3-dibromo-5,5-dimethylhydantoin A-bromosuccinimide A-chlorosuccinimide A-iodosuccinimide neurokinin 1 -methyl-2-pyrrolidinone para-methoxybenzyl polyphosphoric acid Raney Nickel sodium bis(2-methoxyethoxy)aluminum hydride ribonucleic acid 2-(trimethylsilyl)ethoxymethyl nucleophilic substitution on an aromatic ring tetrabutylammonium fluoride tert-butyldimcthyisilyl fert-butyldimethylsilyl trifluoromethanesulfonyl (triflyl) trifluoroacetic acid tri-o-furylphosphine tetrahydrofuran triisopropylsilyl A, N,N ,N -tetramethy lethylenediamine tetramethyl guanidine tetramethylpiperidine trimethylsilyl 2,2 -bis(di-p-tolylphosphino)-l,r-binaphthyl tetrathiafulvalene... 

A carbodiimide-grafted polystyrene resin was reacted with tetramethyl-guanidine to give an interesting biguanide structure (Scheme 13). This was assayed as a catalyst for a transesterification reaction.33 Incidentally, resin-bound guanidines are useful bases for processes involving resin capture.34... 

Schuchardt, U. and Lopes, O.C. 1988. Tetramethyl-guanidine catalyzed transesterification of fats and oils A new method for rapid determination of their composition. JAOCS 65 1940-1941. 

Now for the synthesis. The nitro compound 75 was made from bromopentane and a nitrite in DMSO, a good solvent for Sn2 reactions, and added to the enone 76, an acetal derived from the diketone 74 with the strong base tetramethyl guanidine 77 as catalyst to give the partly protected form 78 of 73. Now all is ready for the various reductions. 

PREPARATION AND REACTIONS OF 2-tert-BUTYL-1,1,3,3-TETRAMETHYL-GUANIDINE 2,2,6-TRIMETHYLCYCLO-HEXEN-1-YL IODIDE... 

To A/iV-dimethyltrimethylacetamido chloride (9) (R = tBu) (6.23 g, 33 mmol) dissolved in dichlorometfaane (50 ml), an ethereal solution of tetramethyl-guanidine (7.79 g, 66 mmol) is added dropwise with stirring. After heating the mixture for 1 h under reflux, the solvent is removed under reduced pressure, and the residue taken up in a little water before addition of a saturated... 

Nitro derivatives 245 were prepared in high yields by Michael addition of primary and secondary nitroalkanes 243 to a, -unsaturated carbonyl derivatives 244 in the presence of DBU in acetonitrile or dimethylformamide (83JAP(K)216144 84S226 85JOC3692). Triethylamine or tetramethyl-guanidine as base proved ineffective or less effective than DBU (84S226). 

Step 3. HWE-modification of the Wittig reaction, tetramethyl-guanidine functions as a base, much like DBU. 

Another example demonstrating the wide application of this procedure is the reaction of 2-bromo-3-oxo-steroids with an excess of diethyl malonate in the presence of 1,1,3,3-tetramethyl-guanidine to form cyclopropanedicarboxylate 5 as well as the cyanocyclopropanemonocar-boxylate 6. The product 6 is formed via nucleophilic displacement of bromine at C2 by a tetramethylguanide moiety. 

Guanidine, 1,1,3,3-tetramethyl- Guanidine, N,N,N, N -tetramethyl-. See Tetramethyl guanidine... 

TMEDA. See 1,3-Diaminopropane N,N,N, N -Tetramethylethylenediamine TMG. See Tetramethyl guanidine TMG acid. See 3,3-Tetramethylene glutaric acid TMI. See p-Tolyl isocyanate m-TMI. Seem-Tolyl isocyanate 3-[(Prop-1-en-2-yl) phenyl] prop-2-yl isocyanate o-TMI. See o-Tolyl isocyanate p-TMI. See p-Tolyl isocyanate TMi (Meta). See 3-[(Prop-1-en-2-yl) phenyl] prop-2-yl isocyanate TML. See Tetramethyl lead TMOS. See Tetramethoxysilane TMP. See Trimethylolpropane 2,3,6-TMP. See 2,3,6-Trimethylphenol 2,4,-TMP. See Isooctane TMPC. See Tetrakis (hydroxymethyl) phosphonium chloride... 

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