Process for preparing nitrooxy esters, nitrooxy thioesters nitrooxy carbonates and nitrooxy thiocarbinates, intermediates useful in said process and preparation thereof

A process for preparing compounds of general formula (III)

• comprising reacting:
• (a) a compound of formula (I)
• RA—H, and (I)
• (b) a compound of formula (II)
• in the presence of dimethylaminopyridine (DMAP), or dimethylaminopyridine (DMAP) and a Lewis acid selected from the group consisting of bismuth triflate and scandium triflate, wherein:
• in formula (I), RA is selected from the group consisting of:
• in formula (II), t is 0 or 1
• W is selected from the group consisting of:
• Y is a bivalent radical having the following meanings:
• a) a straight or branched C1-C20 alkylene, optionally substituted with one or more of the substituents selected from the group consisting of:
• halogen atoms, hydroxy, —ONO2 and T0, wherein T0 is —OC(O)—(C1-C10 alkyl)-ONO2 or —O—(C1-C10 alkyl)-ONO2;
• or a cycloalkylene having from 5 to 7 carbon atoms, wherein the cycloalkylene is optionally substituted with T, wherein T is a straight or branched alkyl with from 1 to 10 carbon atoms;
• or
• wherein:
• n is an integer from 0 to 20,
• n1 is an integer from 1 to 20,
• n2 is 0 or 1;
• wherein the —ONO2 group is linked to —(CH2)n1— group;
• wherein the —ONO2 group is linked to the —(CH2)n6— group;
• wherein the —ONO2 group is linked to the —(CH(R7)— group;
• and
• wherein X2 is O or S,
• n3, n4 and n6 are integer independently selected from 0 to 20,
• n5 is an integer from 0 to 6,
• R6 is H, CH3 or nitrooxy group,
• R7 is CH3 or nitrooxy group,
• wherein:
• n7 is an integer from 0 to 10;
• n8 is an integer from 1 to 10;
• R8 R9, R10, R11 are the same or different, and are H or straight or branched C1-C4 alkyl;
• wherein the —ONO2 group is linked to
• wherein n8 is as defined above
• Y2 is selected from the group consisting of:
• in formula (III), t, RA and X are as above defined.