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For recent reviews on [n]-prismanes, see: (a) Mehta, G. in Strain and Its Implications in Organic Chemistry de Meijere, A.; Blechert, S., Eds. Kluwer Academic Publishers: Dordrecht, 1989, pp 269-281. (b) Mehta, G.; Padma, S. in Carbocyclic Cage Compounds: Chemistry and Applications, Osawa, E.; Yonemitsu, O., Eds. VCH: Weinheim, Germany, 1992, pp 183-215. (c) Forman, M. A.; Dailey, W. P. Org. Prep. & Proc. Int. 1994, 26, 291.
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For recent reviews on [n]-prismanes, see: (a) Mehta, G. in Strain and Its Implications in Organic Chemistry de Meijere, A.; Blechert, S., Eds. Kluwer Academic Publishers: Dordrecht, 1989, pp 269-281. (b) Mehta, G.; Padma, S. in Carbocyclic Cage Compounds: Chemistry and Applications, Osawa, E.; Yonemitsu, O., Eds. VCH: Weinheim, Germany, 1992, pp 183-215. (c) Forman, M. A.; Dailey, W. P. Org. Prep. & Proc. Int. 1994, 26, 291.
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2s photocyclization into a symmetry-forbidden reaction has been proposed, see: Schmidt, W.; Wilkins, B. T. Tetrahedron 1972, 28, 5649.
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For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen- Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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0041605987
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For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen- Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen-Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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28
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0028829824
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For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen- Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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85033140266
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Ref. 7(b)
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For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen- Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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43
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85033132096
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note
-
Taken in part from the theses presented by G.-H. Lin in June 1996, and Y.-L. Yeh in June 1995, to the Chung Cheng University, in partial fulfillment of the requirements for the degree of Master of Science.
-
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44
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0001018308
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51
-
-
85033157387
-
-
note
-
2/THF, reflux) to furnish enediol 26.
-
-
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52
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0000259782
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Steiner, K.5
Widmer, E.6
-
54
-
-
0027182479
-
-
For similar photocyclization, see: Marchand, A. P.; Bott, S. G.; Gadgil, V. R.; Watson, W. H.; Krawiec, M.; Kashyap, R. P. Tetrahedron 1993, 49, 6561.
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Marchand, A.P.1
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Krawiec, M.5
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55
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56
-
-
85033137302
-
-
note
-
We do not think that abstraction of hydrogen atoms from the two hydroxyl groups of an 1,4-diol would occur concurrently to form a bis-alkoxy radical and as an intermediate in the fragmentation reaction. The statement here is only for the purpose of simple description of the overall resulting picture.
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-
-
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58
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0001653721
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(a) Boto, A.; Betancor, C.; Prange, T.; Suarez, E. J. Org. Chem. 1994, 59, 4393.
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Boto, A.1
Betancor, C.2
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64
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0008206426
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Benjamin, W. A.: Menlo Park, California
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(a) House, H. O. Modern Synthetic Reactions; 2nd Ed, Benjamin, W. A.: Menlo Park, California, 1972, p 359-387.
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House, H.O.1
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Silverstein, R.M.1
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67
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0347552917
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(b) Tori, K.; Hata, Y.; Muneyuki, R.; Takano, Y.; Tsuji, T.; Tanida, H. Can. J. Chem. 1964, 42, 926. The chemical shift of olefinic protons in cyclobutene (δ 5.95) verses that of norbomene (δ 5.98) might suggest that this pure fragmentation product is 34 and not 33.
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-
Tori, K.1
Hata, Y.2
Muneyuki, R.3
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Tsuji, T.5
Tanida, H.6
-
68
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85033146771
-
-
Ref. 35a, p 221
-
Ref. 35a, p 221.
-
-
-
-
69
-
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85033157358
-
-
The atomic coordinates, bond lengths, and bond angles for this structure have been deposited at Cambridge Crystallographic Data Center
-
The atomic coordinates, bond lengths, and bond angles for this structure have been deposited at Cambridge Crystallographic Data Center.
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