Hydroxyaminophosphinic acid derivatives

A process for the preparation of a compound of formula Ib comprising the steps of

• a) reaction of a phosphonochloridate of formula II with an O-(trialkylsilyl)hydroxylamine in the presence of a base to give N-[(alkoxy)phosphoryl]hydroxylamines of formula Ia, and
• b) ester cleavage of the compound of formula Ia to give the compounds of the formula Ib
• in which
• T is selected from the group of radicals consisting of the following groups:
• a) straight chain or branched alkyl or alkoxy each having 1 to 20 C atoms, where one or more CH2 groups in these radicals may each be replaced, independently of one another, by —C≡C—CH═CH—,
• —O—, —S—, —CF2O—, —OCF2—, —CO—O—,
• —O—CO—, —SiR0R00—, —NH—, —NR0— or —SO2— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen, CN, SCN or SF5, wherein R0 and R00, identically or differently, denote an alkyl or alkoxy radical having 1 to 15 C atoms, in which, in addition, one or more H atoms may be replaced by halogen,
• b) a three- to ten-membered saturated or partially unsaturated aliphatic ring, in which at least one —CH2— group is replaced with —O—, —S—, —S(O)—, —SO2—, —NRx— or —N(O)Rx—, or in which at least one —CH═ group is replaced with —N═,
• c) a diamondoid radical,
• ZT, Z1, Z2, and Z4, on each occurrence, identically or differently, denote a single bond, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2O—, —OCH2—, —C(O)O—, —OC(O)—, —C(O)S—, —SC(O)—, —(CH2)n1—, —(CF2)n2—, —CF2CH2—, —CH2CF2—,
• —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CH2)n3O—, —O(CH2)n4—, —C≡C—,
• —O—, —S—, —CH═N—, —N═CH—, —N═N—, —N═N(O)—, —N(O)═N— or —N═C—C≡N—, wherein n1, n2, n3, n4,
• identically or differently, are 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
• Z3 denotes —O—, —S—, —CH2—, —C(O)—, —CF2—, —CHF—, —C(Rx)2—, —S(O)— or —SO2—,
• on each occurrence, identically or differently, denote an aromatic, heteroaromatic, alicyclic or heteroaliphatic ring having 4 to 25 ring atoms, which may also contain condensed rings and which may be mono- or polysubstituted by Y,
• denotes an aromatic or heteroaromatic ring having 5 to 25 ring atoms, which may also contain condensed rings and which may be mono- or polysubstituted by RC,
• Y on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF5 or straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
• denotes a group
• wherein the groups may be oriented in both directions,
• L1 to L5, identically or differently, denote H, F, Cl, Br, I, CN, SF5, CF3, OCF3, or OCHF2, where at least one of the present radicals L1 to L5 in the respective groups is not H,
• RL on each occurrence, identically or differently, denotes H, alkyl having 1 to 6 C atoms, alkenyl having 2 to 6 C atoms or alkoxy having 1 to 5 C atoms,
• RC on each occurrence, identically or differently, denotes straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms or cycloalkyl or alkylcycloalkyl each having 3 to 12 C atoms,
• Sp denotes a spacer group or a single bond,
• R0, R00, Rx denote straight-chain or branched alkyl having 1 to 6 C atoms, r, s, t, u and v, identically or differently, are 0, 1 or 2,
• where r+s+t+u+v is 0, 1, 2, 3 or 4, and
• R11 denotes straight chain alkyl having 1 to 12 C atoms or branched alkyl having 3 to 12 C atoms.