Cyclization of 1,1-disubstituted alkenes to cyclopentenes

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9673-9678

  Taber, Douglass F ^a   Christos, Thomas E ^a   Neubert, Timothy D ^a   Batra, Dolly ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BROMINE DERIVATIVE; CARBENE; CYCLOPENTENE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION;

EID: 0033601315     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991311z     Document Type: Article

References (23)

1. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
2. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
3. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
4. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
5. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
6. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
7. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
8. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
9. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
10. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
11. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
12. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
13. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
14. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
15. For leading references to cyclopentene construction by intermolecular C-H insertion of an alkylidene carbene, see: (a) Gilbert, J. C.; Giamualva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 8, 5251. (b) Dreiding, S.; Huguet, J.; Karpf, M. Tetrahedron Lett. 1983, 24, 4177. (c) Gilbert, J. C.; Giamualva, D. H.; Blaze. M. E. J. Org. Chem. 1985, 50, 0, 2557. (d) Ochiai, M.; Kunishima, M.; Tani, S. J. Am. Chem. Soc. 1991, 113, 3135. (e) Taber, D. F.; Walter, R.; Meagley, R. P. J. Org. Chem. 1994, 59, 6014. (f) Tani S.; Kato, A.; Kunishima, M. Tetrahedron Lett. 1994, 35, 7253. (g) Stang, J.; Williamson, B. L.; Tywinski, R. R. J. Am. Chem. Soc. 1994, 116, 93. (h) Taber, D. F.; Walter, R.; Meagley, R. P. Tetrahedron Lett. 1994, 43, 7909. (i) Kim, S.; Cho, C. M. Tetrahedron Lett. 1995, 27, 4845. (j) Ohira, S.; Sawamoto, T.; Yamoto, M. Tetrahedron Lett. 1985, 36, 1537. (k) Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 1, 5723. (l) Taber, D. F.; Christos, T. E. J. Org. Chem. 1996, 61, 2081. (m) Taber, D. F.; Yu, H. J. Org. Chem. 1997, 62, 2, 1687. For reviews, see: (n) Taber, D. F. In Methods of Organic Chemistry; Helmchen, G., Ed.; Georg Thieme Verlag Stuttgart; New York, 1995; Vol. E21; p 1127. (o) Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
16. Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 72, 721.
17. (a) Taber, D. F.; Sahli, A.; Yu, H.; Meagley, R. P. J. Org. Chem. 1995, 60, 6571.
18. For a preliminary account of the cyclization of 1 to 5, see: Taber, D. F.; Christos, T. E. J. Am. Chem. Soc. 1999, 121, 5589.
19. For a summary of the relative rates of insertion into C-H bonds, see: Wolinsky, J.; Clark, G. W. J. Org. Chem. 1976, 41, 745.
20. (a) Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706.
21. (b) Hennessy, M. J. Ph.D. Thesis, University of Delaware, 1998.
22. (c) Stork, G.; Nakatani, K. Tetrahedron Lett. 1995, 36, 1537.
23. Although all of the work described here is based on bromides, we have observed that chlorination followed by exposure to KHMDS works equally well.