References
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- Theron , F. , Verny , M. and Vessiere , R. 1978 . “ Chapter 10 ” . In The Chemistry of the Carbon‐Carbon Triple Bond , Edited by: Patai , S. Chichester : Wiley . Part 1
- Huntsman , W. D. 1980 . “ Chapter 15 ” . In The Chemistry of Ketenes, Allenes and Related Compounds , Edited by: Patai , S. Chichester : Wiley . Part 2
- Wotiz , J. H. 1969 . “ Chapter 7 ” . In Chemistry of Acetylenes , Edited by: Viehe , H. G. New York : Marcel Dekker .
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- Lockwood , R. F. and Nicholas , K. M. 1977 . Tetrahedron Lett. , : 4163
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- Nicholas , K. M. , Mulvaney , M. and Bayer , M. 1980 . J. Am. Chem. Soc. , 102 : 2508
- Padmanabhan , S. and Nicholas , K. M. 1982 . Tetrahedron Lett. , 23 : 2555 For more recent work, see:
- Padmanabhan , S. and Nicholas , K. M. 1983 . Tetrahedron Lett. , 24 : 2239
- Saha , M. and Nicholas , K. M. 1984 . J. Org. Chem. , 49 : 417
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- Maryanoff , B. E. and McComsey , D. F. 1978 . J. Org. Chem. , 43 : 2733
- Nicholas , K. M. and Siegel , J. 1985 . J. Am. Chem. Soc. , 107 : 4999
- Sternberg , H. W. , Greenfield , H. , Friedel , R. A. , Wotiz , J. , Markby , R. and Wender , I. 1954 . J. Am. Chem. Soc. , 76 : 1457
- O‐Yang , C. and Fried , J. 1983 . Tetrahedron Lett. , 24 : 2533 Uncomplexed, the Z and E isomers of 1 were inseparable by tlc. Such cobalt complexes have been reported to facilitate separation of inseparable acetylenic prostaglandins:
- Gribble , G. W. , Leese , R. M. and Evans , B. E. 1977 . Synthesis , : 172
- Anyway, primary acetylenic carbinols are probably the easiest to deoxygenate by conventional techniques without allene production, e. g., see:
- Hutchins , R. O. , Kandasamy , D. , Maryanoff , C. A. , Masalamani , D. and Maryanoff , B. E. 1977 . J. Org. Chem. , 42 : 82
- Hutchins , R. O. , Kandasamy , D. , Dux , F. III , Maryanoff , C. A. , Rotstein , D. , Goldsmith , B. , Burgoyne , W. , Cistone , F. , Dalessandro , J. and Puglis , J. 1978 . J. Org. Chem. , 43 : 2259
- For elimination reactions of cobalt‐acetylenic carbinol complexes, see:
- ref 5, footnote 17
- Connor , R. E. and Nicholas , K. M. 1977 . J. Organometal. Chem. , 125 : C45
- The chemoselectivity of bis(trifluoroacetoxy)borane makes it quite favorable for selective reductions.4
- Mp 152–153°C (2‐propanol); satisfactory C, H, and N analyses
- Maryanoff , B. E. 1984 . J. Med. Chem. , 27 : 843 Prepared according to the styrene oxide procedure in:
- The lactol from phthalide was condensed with Ph3, P=CH(CH2),3COO−Li+ (Maryanoff, B. E. and Duhl‐Emswiler, B. A., Tetrahedron Lett., 1981, 22, 4185), and the product (E/Z = 35:65) was photoisomerized (PhSSPh, sunlamp), esterified (CH3OH, BF3.Et2O), oxidized (pyridinium chlorochromate), and reacted with hexynyl‐magnesium bromide to give 1 (oil; E/Z = 90:10), characterized by 1H NMR and mass spec. (C and H analysis on the parent acid)