3170 volatile compounds were removed in vacuo,12 and T H F ( I O mL) was added to the residue. In a separate flask N i ( p P h 3 ) ~ was prepared from anhydrous Ni(acac)* (1 mmol), diisobutylaluminum hydride ( 1 mmol), triphenylphosphine (4 mmol), and 15 m L of T H F . To the mixture containing the 6-ethoxyethenylzirconium derivative prepared above were added sequentially the supernatant solution of Ni(PPh3)4 and 2.04 g (1 0 mmol) of iodobenzene. After stirring the reaction mixture for 12 h at room temperature, G L C examination of a quenched aliquot indicated the formation of (E)-P-ethoxystyrene in 99% yield. After extraction with diethyl ether, washing with water, and drying, distillation provided I . 12 g (76%) of essentially pure (E)-0-ethoxystyrene: bp 70-72 "C (1.6 mm); ' H N M R (CDC13, Me&) 6 1.27 (t, J = 7 Hz, 3 H), 3.80 (q, J = 7 Hz, 2 H ) , 5.83 (d, J = 13 Hz, 1 H), 6.97 (d, J = 13 Hz, 1 H ) , and 7.20 (broad s, 5 H) ppm; I3C N M R (CDC13, Me4Si) 6 14.80, 65.40, 106.03, 125.11, 125.56, 128.58, 136.68, and 147.96 ppm; IR (neat) 1630 (s), 1180 (s), 930 (m), 920 (m), 750 (s), 690 (s) cm-I.
I . Synthesis of 2,9-Bis(methoxymetl1yl)-2,9-dimethyl-4,7dioxydecanedioic Acid. Scheme
zCH2Br [G ] CH20CH2-
0
CH,
I I CO,H
HJCOCH2-C-CH20CH2-
1
Table I
Acknowledgments. We thank the donors of the Petroleum Research Fund, administered by the American Chemical Society, the National Science Foundation (CHE76-11832 and MPS75-06106), and Syracuse University.
a
References and Notes
C
(9)
(10) (11) (12)
Part 3: E. Negishi, A. 0. King, and N. Okukado, J. Org. Chem., in press. (a) For a review containing pertinent references, see J. Schwartz. J. Organomet. Chem., Library, 1, 461 (1976); (b) D. W. Hart and J. Schwartz, J. Am. Chem. SOC.,96, 81 15 (1974); (c) 0. W. Hart, T. F. Blackburn, and J. Schwartz, ibid., 97, 679 (1975); (d) C. A. Bertelo and J. Schwartz, ibid., 98, 262 (1976). P. W. Collins, E. 2. Dajani, M. S. Bruhn, C. H. Brown, J. R. Palmer, and R. Pappo, Tetrahedron Lett., 4217 (1975). in particular, see footnote 4. After submission of this paper, a paper describing the reaction of organozirconium derivatives with acyl halides via transmetaiationwith aluminum chloride has appeared: D. B. Carr and J. Schwartz. J. Am. Chem. SOC.,99, 638 (1977). We thank Professor J. Schwartz for informing us of these results prior to its publication. (a) E. Negishi and S. Baba, J. Chem. SOC..Chem. Commun., 596 (1976); (b) S. Baba and E. Negishi, J. Am. Chem. Soc., 98, 6729 (1976). References 1 and 5 and references cited therein. The use of 1 equiv each of these reagents has resulted in somewhat diminished and variable yields. A minor amount (
