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3-Methyl-3-oxetanemethanol has been used in the preparation of star-shaped copolymer consisting of a hyperbranched poly(3-methyl-3-oxetanemethanol) core and polytetrahydrofuran arms, pyridyl disulfide-functionalized cyclic carbonate monomer, required for the synthesis of of functional poly(ε-caprolactone) containing pendant pyridyl disulphide groups and δ-lactams. It is used to synthesize octahydroindole alkaloids and γ-butenolides.
Jian Hou and Deyue Yan. Synthesis of a Star-Shaped Copolymer with a Hyperbranched Poly(3-methyl-3-oxetanemethanol) Core and Tetrahydrofuran Arms by One-Pot Copolymerization. Macromolecular Rapid Communications.2002, 23, 456-459.
Bhooma Raghavan; Rodney L Johnson. Short stereoselective synthesis of alpha-substituted gamma-lactams. Journal of Organic Chemistry .2006, 71, (5), 2151-2154.
Reacts with nucleophiles to give 2-substituted 2-methyl-1,3-propanediols; e.g. dialkylamines, on heating under pressure at 180o, give 2-(N,N-dialkylaminomethyl)-2-methylpropane-1,3-diols, and aqueous hydrogen halides give the corresponding 2-halomethyl compounds: Liebigs Ann. Chem., 365 (1973).
Valuable protecting agent for carboxylic acids, introduced by Corey. The oxetane ester, formed from the acid chloride, rearranges with BF3 etherate to the bridged 2,6,7-trioxabicyclo[2.2.2]octane [OBO] orthoester, stable to strong bases and nucleophiles, e.g. Grignards, but readily cleaved by mild acid, followed by saponification of the ester: J. Am. Chem. Soc., 103, 4618 (1991); 106, 2735 (1984); Tetrahedron Lett., 23, 1651 (1982); 24, 5571 (1983); 27, 2199 (1986):
Hazard Statements: H302-H317
Harmful if swallowed. May cause an allergic skin reaction.
Precautionary Statements: P261-P264b-P270-P272-P280g-P301+P312-P302+P352-P330-P333+P313-P363-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant