ChemInform Abstract: Hydroformylation of Aryl Olefins Catalyzed by Rh(acac)(CO)2 Modified with Phosphorus‐Containing Ligands.

Abstract

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Synthesis of Quaternary Carbon Centers via Hydroformylation

“…Though styrenyl-based substrates are known to have a preference for the branched regioisomer,11 α-substituted styrenes have been reported to be highly linear-selective 12. During the course of our studies we found that the branched aldehyde product is unstable to silica gel purification, and also dimerizes to a small extent to a cyclic acetal 13.…”

Synthesis of fragrance compounds from acyclic monoterpenes: Rhodium catalyzed hydroformylation and tandem hydroformylation/acetalization of linalool and β-citronellene

“…Data for 4,8-dimethyl-7(8)-nonenal (2b): MS (70 eV, EI): m/z (%): 168 (2) [M + ], 135 (26), 109 (55), 107 (20), 81 (26), 70 (20), 69 (100), 67 (27), 56 (21), 55 (45). 1 H NMR (400 MHz, CDCl 3 , 25 • C, TMS): ı = 0.89 (d, 3 J = 6.4 Hz, 3H; C 10 H 3 ), 1.12-1.22 (m, 1H; C 4 HH), 1.28-1.38 (m, 1H; C 4 HH), 1.40-1.50 (m, 2H; C 3 H and C 2 HH), 1.60 (s, 3H; C 8 H 3 ), 1.68 (s, 3H; C 9 H 3 ), 1.65-1.75 (m, 1H; C 2 HH), 1.90-2.05 (m, 2H; C 5 H 2 ), 2.38-2.48 (m, 2H; C 1 H 2 ), 5.09 (t, 3 J = 7.0 Hz, 1H; C 6 H), 9.77 ppm (t, 3 J = 1.8 Hz, 1H; CHO).…”

“…Although the hydroformylation of more abundant monoterpenes, such as limonene, ␤-pinene, myrcene and camphene, was quite extensively studied [11][12][13][14][15][16][17][18][19][20], only few reports appeared on the hydroformylation of linalool [11,[21][22][23] and ␤-citronellene (dihydromyrcene) [11,24,25]. Linalool, a monoterpenoid allylic alcohol with a pleasant lily odor, is a key building block for the synthesis of various vitamins and fragrances, such as vitamin A, vitamin E, citral and citronellol [3,4].…”