Coordination Chemistry of Ester-Functionalized Cp\nLigands. The Atom-Economy Synthesis of\nNa[C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>(CH<sub>2</sub>)<sub>2</sub>OH] and Solid State Structures of\n[Rh{C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>(CH<sub>2</sub>)<sub>2</sub>OH}(CO)<sub>2</sub>] and\n[Rh<sub>2</sub>{μ-(C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>}(NBD)<sub>2</sub>]
Luigi Busetto (2095507)M. Cristina Cassani (2162242)Vincenzo G. Albano (2714695)Piera Sabatino (1504804)
Abstract
The one-step synthesis of Na[C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>CH<sub>2</sub>CHCH<sub>2</sub>] (<b>1</b>) from NaCp and diallyl carbonate\nis presented together with a simple pathway for the synthesis of sodium hydroxyalkoxycarbonylcyclopentadienide, Na[C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>(CH<sub>2</sub>)<sub>2</sub>OH] (<b>2</b>). The latter new reagent is obtained\nin high yield by reacting NaCp with 1,3-dioxolan-2-one (ethylene carbonate). When (±)-4-methyl-1,3-dioxolan-2-one [(±)-1,2-propylene carbonate] is used, the ring-opening reaction\nleads to a mixture of the two regioisomers Na[C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>CH<sub>2</sub>CH(Me)OH] (<b>3a</b>) and Na[C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>CH(Me)CH<sub>2</sub>OH] (<b>3b</b>) in a 7:3 ratio. Reactions of <b>1</b> and <b>2</b> with FeCl<sub>2</sub> and [Rh(L,L)Cl]<sub>2</sub>\n[L,L = CO or L,L = 2,5-norbornadiene (NBD)] lead to the respective metal complexes [Fe(C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>CH<sub>2</sub>CHCH<sub>2</sub>)<sub>2</sub>] (<b>4</b>), [Fe{C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>(CH<sub>2</sub>)<sub>2</sub>OH}<sub>2</sub>] (<b>5</b>), [Rh(C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>CH<sub>2</sub>CHCH<sub>2</sub>)(CO)<sub>2</sub>]\n(<b>6</b>), [Rh{C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>(CH<sub>2</sub>)<sub>2</sub>OH}(CO)<sub>2</sub>] (<b>7</b>), and [Rh{C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>(CH<sub>2</sub>)<sub>2</sub>OH}(NBD)] (<b>8</b>). Additionally\nin the reaction of <b>2</b> with [Rh(L,L)Cl]<sub>2</sub> the diester-bridged dinuclear adducts [Rh<sub>2</sub>{μ-(C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>}(L,L)<sub>2</sub>] [L,L = CO (<b>9</b>); L,L = NBD (<b>10</b>)] are isolated. The reaction of <b>2</b> with MBr(CO)<sub>5</sub> (M = Mn, Re) leads to [M{C<sub>5</sub>H<sub>4</sub>CO<sub>2</sub>(CH<sub>2</sub>)<sub>2</sub>OH}(CO)<sub>3</sub>] [M = Mn (<b>11</b>); M = Re (<b>12</b>)]\ntogether with a complex mixture of unidentified metal carbonyls. The X-ray molecular\nstructures of <b>7 </b>and <b>10</b> are reported.
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