AMMO monomer

The energetic nature of the azido group makes its incorporation into energetic polymers and binders very desirable. 3,3-Bis(azidomethyl)oxetane (BAMO) (28) and 3-azidomethyl-3-methyloxetane (AMMO) (33) are energetic monomers which on polymerization result in the energetic polymers poly[BAMO] (32) and Poly[AMMO] (34), respectively, both of which are under evaluation as potential energetic alternatives to HTPB in composite propellant formulations. ... 

Scheme 16 Synthesis of 5-ammo-6-deoxy- or 6-amino-6-deoxyaldomc acid monomers...

The synthesis of AMO involves treatment of 3,3-bis(chloromethyl) oxetane (BCMO) with sodium azide in the DMF medium at 85 °C for 24 h. Similarly, AMMO which is a monofunctional analog of AMO is synthesized by the azidation of chloro/tosylate product of 3-hydroxymethyl-3-methyl oxetane (HyMMO) with sodium azide in DMF medium at elevated temperatures. These energetic monomers are readily polymerized to liquid curable prepolymers with the help of boron trifluoride etherate/l,4-butanediol initiator system and the outlines of synthesis [147-150] of poly(BAMO) [Structure... 

Copolymers of acrylamide and acryioyloxyethyltrimethyl ammo ilium chloride have become increasingly preferred due to the favorable reactivity ratios between these two monomers, which result in copolymers witli a uniform composition. 

Poly-AMMO is synthesized via cationic polymerisation from the monomer 3-azidomethyl-methyl-oxetane (AMMO). The polymerisation reaction is quenched with water to get polymer chains with hydroxyl endgroups which enable to react these pre-polymers later with isocyanate for curing reaction. Poly-AMMO is suggested as - energetic binder component in -< composite propellants and is in the scope of actual research. 

This process for cationic polymerization of lactams has been studied extensively. Figure 2.1 shows the principal reactions of monomer conversion and chain growth [27]. Mechanistically, chain growth can commence on both the ammo-terminal end via acylation and the carboxy-terminal end via aminolysis of the polymer molecule. High extents of polymerization are rarely attained because of the occurrence of side-reactions. As shown in Figure 2.2 [27] these side-reactions result in terminal amidine groups that are incapable of adding further lactam. The cationic polymerization process has therefore not attained any practical importance. 

N2 is also present. No doubt, the decomposition process begins in the methylazide group [10]. Fast thermolysis of the azidomethyl oxetane monomers that polymerize to form AMMO and BAMO yields products that are... 

Two useful derivatives whose syntheses are not described here are the 2 -<7-allylinosine monomer (13,14), and the 2 -6 -allyl-2-amino-adenosine monomer (13,14). The 2 -0-allylinosine monomer is obtained from compound 12 by desilylation, oximate reaction (requires 24 h reflux in acetonitrile), and dimethoxytritylation followed by phosphitylation. The 2 -0-allyl-2-aminoadenosine monomer is obtained from compound 20 by protection of the exocyclic ammo groups followed by desilylation, dimethoxytritylation, and finally phosphitylation. 

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