solution and a mixture of 5 or 6 and protonated pyridine precipitated. The latter was removed by fractional recrystallization from CH,CI,!Et,O.
Synthesis of 5 and 6 from 2: A solution of 2.5 mmol of 2 in 20 mL of CH,CI, was treated with 2 5 inmol of Me,SiOTf. Then 6 mmol of diazo ester 3 or 4 was added dropui\e. which was accompanied by release of N,. 30 min after N, release had stopped. Et,O \bas added and 5 or 6 precipitated. Both compounds were removed by liltrntion. washed, and dried at 0.01 Torr. Synthesis of7 ~ 12: A solution of 2 mmol of 6 in 20 mL of CH,CI, was treated with 2.5 mmol oi'the appropriate nucleophile. Alier 1 h the corresponding products were precipitated by addition of EtzO. removed by filtration, washed with Et,O. and dried i l l 0 01 Torr. Table 1 analyses were d s o obtained. Yields and spectroscopic data of compounds 5 1 2 [a]. Correct C,H.N 5 Yellow powder: yield: 84% [b]; ' H NMR (CD,CN): 6 = 1.46 (s. 9 H ; CH,). 7.58 (t. 2 H . H-3:H-5 Ph). 7.75 (t. 1 H ; H-4 Ph), 8.10 id. 2 H ; H-2!H-6 Ph): ' T N M R (CD,CN) [c]: 6 = 28.14 (CH,). 87.00 (C(CH,),). 117.63 (C-l Ph), 121.70 (9. ' J ( C . F ) = 320 HL; CF,), 133.05 (C-3;C-5 Ph), 134.25 (C-4 Ph). 136.24 (C-2;C-6 Ph). 161) 86 (COI: I R : 3[cm-'] = 2100 (N,). 1700 (CO). 6 Yellowpowder,?.ield: 81% [b]; ' H N M R ( C D , C N ) : 6 =1.25(1.3H;CH,).4.28 (q. 2 H , CH2).7.5X (t. 2 H : H-3/H-5 Ph). 7.74(t, 1 H: H-4 Ph). 8.13 (d. 2 H ; H-2iH-6 Ph); "C'NMR (CD,CN) [c]: S ~1 4 . 4 9 (CH,). 65.14 (CH,). 117.71 (C-l Ph). 121.65 (q. ' J ( C . F ) = 320 Hz; CF,), 133.04 (C-3:C-5 Ph). 134.33 (C-4 Ph), 136.47 (C-?:C-6 Ph). 162.12 ( C O ) : IR: G[cin-'] = 2100 (N2). 1710 (CO). 7: Yellou,powder:yield:74%; 'HNMR(CD,CN):d =1.30(t.3H;CH,),4.35(q. ZH,CH,). X.20(t,2H:H-3/H-5pyridine).8.72(t,lH; H-4pyridine). 8.90(d,ZH; H-2:H-6 pyridine): "CNMR (CD,CN) [cl: 6 =14.57 (CH,). 64.13 (CH,), 122.00
(q, ' J ( C . F ) = 320 Hr: CF,). 130.00 (C-3.C-5 pyridine). 149.54 (C-4 pyridine). 150.25 i C ' -2 C 6 pyridine), 161.35 (CO). i.[cm-'] = 2115 (Nz). 1710 (CO). 8~Colorle.;apowder:yield:90%:'HNMR(CDCI,):fi =1.35(1. 3H;OCH2CH,).
3.33 (5. 6 H : S(CH,),). 4.35 (q, 2 H ; OCH2CH,); ',CNMR (CDCI,): 6 =14.08 (0CH:C.H %). 27.53 (S(CH,),). 55.10 (CNI). 63.40 (OCH,CH,). 120.46 (4, 'J(C7.F) = 320 Hz: CF,), 160.29 ( C O ) . IR. ?[cm-'] = 2140 (N2). 1695 (CO). 9: Light?cllowpowder;yield: 95%: 'HNMR(CDCI,):6 =1.20(t.3H:CH3).4.27 ( q . 4 H : C H J . 7.78lmc, 15H;AsPhJ: "CNMR (