References
- Babler , J. H. and Olsen , D. O. 1974 . Tetrahedron Lett. , : 351 and references therein
- Bergmann , E. D. 1951 . J. Am. Chem. Soc. , 73 : 1218
- Buehler , C. A. and Pearson , D. E. 1970 . Survey of Organic Syntheses , 604 New York : John Wiley & Sons, Inc. .
- Seward, Illinois : Available from Apache Chemicals, Inc. . 61077
- Trost , B. M. and Stanton , J. L. 1975 . J. Am. Chem. Soc. , 97 : 4018 For a discussion of other methods developed to effect this same transformation, see, and references therein
- Faulkner , D. J. 1971 . Syntheses , : 175 For two recent reviews, see, and J. Reucroft and P. J. Sammes, Quart. Rev., Chem. Soc., 25, 135 (1971)
- Available from Aldrich Chemical Company, Inc., Milwaukee, Wisconsin 53233
- Corey , E. J. and Suggs , J. W. 1975 . Tetrahedron Lett. , : 2647
- The 3° alcohols (2) were prepared by dropwise addition of a 1 M ether solution of the corresponding ketone (1) to a 15% excess of a 2.3 M solution of vinylmagnesium chloride in THF at 0°C. For a previous report of the preparation of these same carbinols (2), see reference 1
- A 6′ × 1/8″ SE-30 column (oven temp = 148°C, tR = 5.5 min) was used for this analysis
- Locquin , R. and Wouseng , S. 1922 . Compt. rend. , 174 : 1711
- This ratio was determined via both NMR and VPC analysis (SE-30 column) of the aldehyde product. Confirmation of the assigned structure was obtained by comparison (NMR and VPC) with an authentic sample of citral. The E stereoisomer was characterized by a doublet at 9.90δ (J=7.5 Hz, CHO), whereas the corresponding signal for the Z stereoisomer was 9.80 δ (doublet, J = 7.5 Hz, CHO)
- Corey , E. J. , Ensley , H. E. and Suggs , J. W. 1976 . J. Org. Chem. , 41 : 380
- Identified by comparison (NMR and VPC) with an authentic sample of acetophenone
- Ficini , J. and Normant , H. 1958 . Compt. rend. , 247 : 1627 Identified by comparison of its properties (bp; mp of 2,4-DNP derivative) with those previously reported for this aldehyde. See, The E stereoisomer was characterized by NMR absorption at 2.51δ (vinyl CH3), whereas the corresponding signal for the Z stereoisomer appeared at 2.25 δ
- Vodoz , C. A. and Schinz , H. 1950 . Helv. Chim. Acta , 33 : 1321
- This ratio was determined by NMR analysis. The spectral properties of this aldehyde mixture were identical to those previously reported18 for the same compound
- Tumlinson , J. H. , Gueldner , R. C. , Hardee , D. D. , Thompson , A. C. , Hedin , P. A. and Minyard , J. P. 1971 . J. Org. Chem. , 36 : 2616 For other syntheses of the cyclohexyl constituents of the boll weevil sex pheromone, see, J. H. Babler and T. R. Mortell, Tetrahedron Lett., 669 (1972); R. H. Bedoukian and J. Wolinsky, J. Org. Chem., 40, 2154 (1975): and S. W. Pelletier and N. V. Mody, J. Org. Chem., 41, 1069 (1976)