Abstract
Strain in an organic molecule often correlates with increased reactivity, at least for certain types of reactions. Thus, the elucidation of the chemistry of highly strained alkenes like the unusual tetrasubstituted alkene, bicyclopropylidene (1), which is a particularly strained derivative of methylenecyclopropane (2), has proved to be fruitful both with respect to synthetic applications as a C6 building block, as well as understanding certain reaction principles. The different, steadily improved methods which have been developed for the preparation of this unusual alkene in the last thirty years as well as rather recent methods for the synthesis of functionally substituted, and spirocyclopropanated derivatives as well as bis(bicyclopropylidenyls) are presented. The special aspects of molecular geometry in bicyclopropylidenes as well as strain and its influence on chemical properties are discussed.The rich chemistry of bicyclopropylidene beginning with its well-known thermal rearrangement and dimerization, its dihalocarbene additions all the way to its recently developed organometallic chemistry, especially its reactions under the catalysis of palladium and other transition metals, is covered. Finally, some synthetically useful chemical transformations of bicyclopropylidene derivatives, e.g., synthetic approaches to the cyclopropanated analogs of natural products, are presented.
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References
Le Perchec P, Conia J-M (1970) Tetrahedron Lett 1587
(a) Binger P, Büch HM, Top Curr Chem (1987) 135:77; (b) Binger P, Schmidt T (1997) In: de Meijere A (ed) Houben-Weyl, Thieme, Stuttgart, Vol E 17c, p 2217; (c) Brandi A, Goti A (1998) Chem Rev 98:589
Denis JM, Le Perchec P, Conia J-M (1977) Tetrahedron 33:1587
(a) de Meijere A (1971) Habilitationsarbeit, Universität Göttingen; (b) de Meijere A (1974) Chem Ber 107:1702
Denis JM, Girard C, Conia J-M (1972) Synthesis 549
Zefirov NS, Lukin KA, Politanskii SF, Margulis MA (1987) Zh Org Khim 23:1799; J Org Chem USSR (Engl Transl) 23:1603
(a) Schipperijn AJ (1971) Recl Trav Chim Pays-Bas 90:1110; (b) Schipperijn AJ, Smael P (1973) Recl Trav Chim Pays-Bas 92:350
Kaufmann D, de Meijere A (1984) Chem Ber 117:3134
Fitjer L, Conia J-M (1973) Angew Chem 85:347; Angew Chem Int Ed Engl 12: 332
Weber W, de Meijere A (1986) Synth Commun 16:837
Schmidt AH, Schirmer U, Conia J-M (1976) Chem Ber 109:2588
Lukin KA, Kuznetsova TS, Kozhushkov SI, Piven’ VA, Zefirov NS (1988) Zh Org Khim 24:1644; J Org Chem USSR (Engl Transl) 24:1483
Kulinkovich OG, Sviridov SV, Vasilevski DA (1991) Synthesis 234
(a) de Meijere A, Kozhushkov SI, Spaeth T, Zefirov NS (1993) J Org Chem 58:502; (b) de Meijere A, Kozhushkov SI, Spaeth T (1999) Org Synth accepted for checking
Moore WR, Ward HR (1960) J Org Chem 25:2073; for the really first, but unverified, communication about the preparation of a bicyclopropylidene derivative see: Kohler EP, Darling SF (1930) J Am Chem Soc 52:424
Fukuda Y, Yamamoto Y, Kimura K, Odaira Y (1979) Tetrahedron Lett 877
Molchanov AP, Kalyamin SA, Kostikov RR (1992) Zh Org Khim 28:122; Russ J Org Chem (Engl Transl) 28:102
Ando T, Muranaka T, Ichihara T (1981) Bull Chem Soc Japan 54:3227
Marquis ET, Gardner PD (1966) J Chem Soc Chem Commun 726
Köbrich G, Goyert W (1968) Tetrahedron 24:4327
Moore WR, Bach RD (1972) J Am Chem Soc 94:3148
Christ M, Moigno D, Peters E-M, Peters K, von Schnering HG (1997) Liebigs Ann/Recueil 1791
(a) Taylor KG, Chaney J (1972) J Am Chem Soc 94:8924; (b) Taylor KG, Chaney J, Deck JC (1976) J Am Chem Soc 98:4163
Pilidis G (1986) Collect Czech Chem Commun 51:2151
Banwell MG, Gabbe RW, Greenwood RJ, Lambert JN, McKay MF, Walter JM (1997) Synlett 953
Seyferth D, Massol M, Barrau J, Monteverdi S (1980) J Organomet Chem 185:307
Warner P, Chang S-C, Powell DR, Jacobson RA (1981) Tetrahedron Lett 22:533
Neidlein R, Pognee V, Kramer W, Glück C (1986) Angew Chem 98:735; Angew Chem Int Ed Engl 25:731; Such type of compounds are essentially derivatives of cycloproparenes, for the reviews see: (a) Halton B (1989) Chem Rev 89:1161, (b) Halton B, Stang PJ (1987) Acc Chem Res 20:443; (c) Müller P (1997) In: de Meijere A (ed) Houben-Weyl, Thieme, Stuttgart, Vol E 17d, p 2865; (d) Halton B, Banwell MG (1987) In Rappoport Z (ed) The Chemistry of a Cyclopropyl Group, Wiley, Chichester, p 1223
(a) Banwell MG, Hockless DCR, Walter JM (1996) J Chem Soc Chem Commun 1469; (b) Banwell MG, Hockless DCR, Longmore RW, Walter JM (1997) Aust J Chem 50:547
Osterodt J, Vögtle F (1996) J Chem Soc Chem Commun: 547; for the alternative approach to this compound see also: Fabre TS, Treleaven WD, McCarley TD, Newton CL, Landry RM, Saraiva MC, Strongin RM (1998) J Org Chem 63:3522
Bertrand M, Tubul A, Ghiglione C (1983) J Chem Res Miniprint 2274
For reviews on the transformation of dibromocyclopropanes to allenes (see so-called Doering-Skattebøl-Moore reaction) see: (a) Hopf H (1980) In: Patai S (ed) The Chemistry of Ketenes, Allenes and Related Compounds Wiley, New York, Part 2, Chapter 2, p 779; (b) Lee-Ruff E (1997) In: de Meijere A (ed) Houben-Weyl, Thieme, Stuttgart, Vol E 17c, p 2388; (c) Backes J, Brinker UH (1989) In Regitz M (ed) Houben-Weyl, Thieme, Stuttgart, Vol E 19b, p 391
Zöllner S (1991) Dissertation, Universität Hamburg
(a) Lukin KA, Zefirov NS, Yufit DS, Struchkov YuT (1992) Tetrahedron 45:9977; (b) Averina EB, Kuznetsova TS, Zefirov AN, Koposov AE, Grishin YuK, Zefirov NS (1999) Mendeleev Commun 101
(a) Holm KH, Mohamed EA, Skattebøl L (1993) Acta Chem Scand 47:500; (b) Brun R, Grace DSB, Holm KH, Skattebøl L (1986) Acta Chem Scand B 40:21
(a) Anderson HW (1972) PhD Thesis, Massachusetts Institute of Technology, Cambridge, Massachusetts; (b) Egge R (1981) Diplomarbeit, Universität Hamburg
Bräse S, de Meijere A (unpublished results)
Arct J, Skattebøl L (1982) Acta Chem Scand B 36:593
Tverezovsky VV, Baird MS, Bolesov IG (1997) Tetrahedron 43:14773
(a) Borer M, Loosli T, Neuenschwander M (1991) Chimia 45:382; (b) Loosli T, Borer M, Kulakowska I, Minder A, Neuenschwander M, Engel P (1995) Helv Chim Acta 78:1144; (c) Borer M, Loosli T, Minder A, Neuenschwander M, Engel P (1995) Helv Chim Acta 78:1311
Skattebøl L (1965) Tetrahedron Lett 2175
Kostikov RR, Vasil’eva IA, Slobodin YaM (1974) Zh Org Khim 10:2325; J Org Chem USSR (Engl Transl) 10:2339
(a) Jochims JC, Karich G (1974) Tetrahedron Lett 4215; (b) Karich G, Jochims JC (1977) Chem Ber 110:2680
Dehmlow EV, Schönefeld J (1971) Justus Liebigs Ann Chem 744:42
(a) du Laurens B, Bezaguet A, Davidovich G, Bertrand M, Chouteau J (1967) Bull Soc Chim France 799; (b) Bezaguet A, Bertrand M (1965) CR Hebd Seances Acad Sci 261:1695
Kostikov RR, Molchanov AP, Vasil’eva IA, Slobodin YaM (1977) Zh Org Khim 13:2541; J Org Chem USSR (Engl Transl) 13:2361
Billups WE, Haley MM, Boese R, Bläser D (1994) Tetrahedron 50:10693
Köbrich G, Heinemann H, Zündorf W (1967) Tetrahedron 23:565
Crandall JK, Paulson DR, Bunnell CA (1969) Tetrahedron Lett 4217
Paulson DR, Crandall JK, Bunnell CA (1970) J Org Chem 35:3708
Dolbier WR, Alonso JH (1973) J Am Chem Soc 95:4421
Lukin KA, Masunova AYu, Kozhushkov SI, Kuznetsova TS, Ugrak BI, Piven’ VA, Zefirov NS (1991) Zh Org Khim 27:488; J Org Chem USSR (Engl Transl) 27:422
Lukin KA, Kozhushkov SI, Andrievsky AA, Ugrak BI, Zefirov NS (1991) J Org Chem 56:6176
de Meijere A, Kozhushkov SI, Zefirov NS (1993) Synthesis 681
Brandl M, Kozhushkov SI, Yufit DS, Howard JAK, de Meijere A (1998) Eur J Org Chem 2785
(a) von Seebach M (1997) Diplomarbeit, Universität Göttingen; (b) von Seebach M, Kozhushkov SI, Benet-Buchholz J, Boese R, de Meijere A, unpublished results
Löhr S (1997) Diplomarbeit, Universität Göttingen
Heiner T, Kozhushkov SI, Noltemeyer M, Haumann T, Boese R, de Meijere A (1996) Tetrahedron 52:12185
de Meijere A, Khlebnikov AF, Kostikov RR, Kozhushkov SI, Schreiner PR, Wittkopp A, Yufit DS (1999) Angew Chem in press; Angew Chem Int Ed Engl in press
Doering WvE, Roth WR (1963) Tetrahedron 19:715
Furukawa J, Kawabata N, Nishimura J (1968) Tetrahedron 24:53
Kirmse W, Schütte H (1968) Chem Ber 101:1674
Fitjer L, Conia J-M (1973) Angew Chem 85:832; Angew Chem Int Ed Engl 12:761
Zöllner S, Buchholz H, Boese R, Gleiter R, de Meijere A (1991) Angew Chem 103:1544; Angew Chem Int Ed Engl 30:1518
Zefirov NS, Kozhushkov SI, Ugrak BI, Lukin KA, Kokoreva OV, Yufit DS, Struchkov YuT, Zoellner S, Boese R, de Meijere A (1992) J Org Chem 57:701
Fitjer L (1976) Angew Chem 88:803; Angew Chem Int Ed Engl 15:763
Fitjer L (1982) Chem Ber 116:1035
Donskaya NA, Akhachinskaya TV, Leonova TV, Shulishov EV, Shabarov YuS (1980) Zh Org Khim 16:563; J Org Chem USSR (Engl Transl) 16:487
Kuznetsova TS, Averina EB, Kokoreva OV, Zefirov AN, Grishin YuK, Zefirov NS (1999) sZh Org Khim in press
Averina EB, Kuznetsova TS, Zefirov AN, Grishin YuK, Zefirov NS (1999) Dokl Akad Nauk 364:61; Dokl Chem (Engl Transl) 364:1
Garratt PJ, Tsotinis A (1990) J Org Chem 55:84
Kuznetsova TS, Eremenko OV, Kokoreva OV, Averina EB, Zefirov AN, Zefirov NS (1997) Zh Org Khim 33:916; Russ J Org Chem (Engl Transl) 33:849
Lord RC, Warrey CJ (1973) Spectrochim Acta A 30:915
Hofland A, Steinberg H, de Boer TJ (1985) Recl Trav Chim Pays-Bas 104:350
Courtieu J, Gounelle Y, Jullien J, Barnier JP, Conia J-M, Kan SK (1982) Org Magn Res 19:63
Schonk RM, Meijer CW, Bakker BH, Zöllner S, Cerfontain H, de Meijere A (1993) Recl Trav Chim Pays-Bas 112:457
(a) de Meijere A, Kozhushkov S (1995) In: Halton B (ed) Advances in Strain in Organic Chemistry, JAI Press Ltd, Greenwich, Vol 4, p 225, and references cited therein; (b) de Meijere A, Kozhushkov SI (2000) Chem Rev 100: in press
Gerson F, de Meijere A, Qin X-Z (1989) J Am Chem Soc 111:1135
Gerson F, Schmidlin R, de Meijere A, Späth T (1995) J Am Chem Soc 117:8431
Gleiter R, Haider R, Conia J-M, Barnier J-P, de Meijere A, Weber W (1979) J Chem Soc Chem Commun 130
Hofland A, de Boer TJ (1987) Recl Trav Chim Pays-Bas 106:558
(a) Gleiter R, Spanget-Larson J (1992) In: Halton B (ed) Advances in Strain in Organic Chemistry JAI Press Ltd, London, Vol 2, p 143; (b) Gleiter R, Kozhushkov SI, de Meijere A unpublished results
Trætteberg M, Simon A, Peters EM, de Meijere A (1984) J Mol Struct 118:333
de Boer JSAM, Stam CH (1993) Recl Trav Chim Pays-Bas 112:635
Boese R, Haumann T, Kozhushkov SI, de Meijere, to be published
Boese R, Haumann T, Stellberg P (1995) In: Hargittai M, Hargittai I (eds) Advances in Molecular Structure Research JAI Press Ltd, London, Vol 1, p 202 and references therein
Boese R, Haumann T, Jemmis ED, Kiran B, Kozhushkov SI, de Meijere A (1996) Liebigs Ann 913
Randic M, Jakab L (1971) Croat Chem Acta 43:145
Eckert-Macsic M, Maksic ZB, Skanske A, Skanske PN (1987) J Phys Chem 91:2786
Randic M, Kumar L (1975) J Mol Struct 26:145
Boese R (1992) In Halton B (ed) Advances in Strain in Organic Chemistry JAI Press Ltd, London, Vol 2, p 191
Greenberg A, Liebman JF (1978) Strained Organic Molecules, Organic Chemistry Series, Vol 38, Academic Press, New York
(a) Cremer D, Kraka E (1988) In: Liebman JF, Greenberg A (eds) Structure and Reactivity VCH, Weinheim, p 65 and references cited therein; (b) Schulman JM, Disch RL (1985) Chem Phys Lett 113:291
Schleyer PvR, Williams JE, Blanchard KR (1970) J Am Chem Soc 92:2377
Beckhaus H-D, Rüchardt C, Kozhushkov SI, Belov VN, Verevkin SP, de Meijere A (1995) J Am Chem Soc 117:11854 and references cited therein
Kuznetsova TS (1991) Habilitation Thesis, Moscow State University
Domalski ES, Hearing ED (1988) J Phys Chem Ref Data 17:1637
(a) Bushby RJ, Jesudason MV, Pollard MD, Shuhaibar KF (1982) J Chem Soc Perkin Trans 1 2647; (b) Bushby RJ, Mann S, Jesudason MV (1984) J Chem Soc Perkin Trans 1 2457; c) Bushby RJ, Mann S, Jesudason MV (1983) Tetrahedron Lett 24:4743
Dolbier WR, Akiba K, Bertrand M, Bezaguet A, Santelli M (1970) J Chem Soc D717
Dolbier WR, Akiba K, Riemann JM, Harmon CA, Bertrand M, Bezaguet A, Santelli M (1971) J Am Chem Soc 93:3933
Dolbier WR (1968) Tetrahedron Lett 393
Gajewski JJ (1981) In Hydrocarbon Thermal Isomerizations, Academic Press, New York, p 149; for the mechanism of this reaction see also ref. [104]
(a) Faber D (1996) Dissertation, Universität Götingen; (b) Faber D, de Meijere A unpublished results, (c) Kozhushkov SI, de Meijere A (1997) In: de Meijere A (ed) Houben-Weyl, Vol E 17b, Thieme, Stuttgart, p 1697
de Meijere A, Erden I, Weber W, Kaufmann D (1988) J Org Chem 53:152
Fitjer L, Conia J-M (1973) Angew Chem 85:349; Angew Chem Int Ed Engl 12:334
Belov VN, Kozhushkov SI, Yufit DS, de Meijere A unpublished results
Lukin KA, Zefirov NS (1991) Zh Org Khim 27:1358; J Org Chem USSR (Engl Transl) 27:1187
de Meijere A, Kozhushkov SI, Haumann T, Boese R unpublished results
Miyashi T, Takahashi Y, Ohaku H, Ikeda H, Morishima S (1991) Pure Appl Chem 63:223
Fitjer L (1975) Angew Chem 87:381; Angew Chem Int Ed Engl 14:360
Reviews: (a) Subramanian LR, Zeller K-P (1997) In: de Meijere A (ed) Houben-Weyl, Vol E 17a Thieme, Stuttgart, p 256; (b) Simmons HE, Cairns TL, Vladuchik SA, Hoiness CM (1973) Org React 20:1
Lukin KA, Kuznetsova TS, Kozhushkov SI, Piven’ VA, Zefirov NS (1988) Zh Org Khim 24:1644; J Org Chem USSR (Engl Transl) 24:1483
Lukin KA, Zefirov NS (1989) Dokl Akad Nauk SSSR 305:631; Dokl Chem (Engl Transl) 305:104
Lukin KA, Andrievskii AA, Zefirov NS (1991) Dokl Akad Nauk SSSR 321:521; Dokl Chem (Engl Transl) 321:353
Lukin KA, Zefirov NS (1987) Zh Org Khim 23:2548; J Org Chem USSR (Engl Transl) 23:2249
(a) Miyazawa K, de Meijere A unpublished results; (b) Moss R, de Meijere A unpublished results
Kozhushkov SI, Haumann T, Boese R, de Meijere A (1993) Angew Chem 105:426; Angew Chem Int Ed Engl 32:401
Kostikov RR, Molchanov AP, Komendantov MI (1979) Zh Org Khim 15:1437; J Org Chem USSR (Engl Transl) 15:1282
Späth T (1995) Dissertation, Universität Göttingen
Tubul A, Bertrand M (1984) Tetrahedron Lett 25:2219
Yufit DS, Struchkov YuT, Kozhushkov SI, de Meijere A (1995) Acta Crystallogr C 51:1325
Zefirov NS, Lukin KA, Kozhushkov SI, Kuznetsova TS, Domarev AM, Sosonkin IM (1989) Zh Org Khim 25:312; J Org Chem USSR (Engl Transl) 25:278
Erden I (1986) Synth Commun 16:117
Lukin KA, Andrievskii AA, Zefirov NS, Masunova AYu (1991) Dokl Akad Nauk SSSR 316:379; Dokl Chem (Engl Transl) 316:19
de Meijere A, Kozhushkov SI, Yufit DS, Boese R, Haumann T, Pole DL, Sharma PK, Warkentin J (1996) Liebigs Ann 601
de Meijere A, Kozhushkov SI, Yufit DS, Howard JAK (1999) Mendeleev Commun 5
Kaufmann D, de Meijere A (1973) Angew Chem 85:151; Angew Chem Int Ed Engl. 12:159
Thiemann T, Rauch K, de Meijere A unpublished results
Buback M, Heiner T, Hermans B, Kowollik C, Kozhushkov SI, de Meijere A (1998) Eur J Org Chem 107
Weber W, Erden I, de Meijere A (1980) Angew Chem 92:387; Angew Chem Int Ed Engl 19:387
de Meijere A, Wenck H, Seyed-Mahdavi F, Viehe HG, Gallez V (1986) Tetrahedron 42:1291
Schonk RM, Bakker BH, Cerfontain H (1991) Phosph Sulf Sil Relat Elem 59:467
Kuznetsova TS, Kozhushkov SI, Lukin KA, Grishin YuK, Bazhenov DV, Koz’min AS, Zefirov NS (1991) Zh Org Khim 27:78; J Org Chem USSR (Engl Transl) 27:67
Späth T, Kozhushkov SI, Fiebig T, Ruasse M-F, Dodin M, Albrecht K, Apeloig Y, de Meijere A (1999) J Org Chem submitted
Kozhushkov SI, Brandl M, de Meijere A (1998) Eur J Org Chem 1535 and references cited therein
Brandi A, Goti A, Kozhushkov SI, de Meijere A (1994) J Chem Soc Chem Commun 2185
Goti A, Anichini B, Brandi A, Kozhushkov SI, Gratkowski C, de Meijere A (1996) J Org Chem 61:1665
(a) Anichini B, Goti A, Brandi A, Kozhushkov SI, de Meijere A (1997) Synlett 25; (b) Goti A, Anichini B, Brandi A, de Meijere A, Citti L, Nevischi S (1995) Tetrahedron Lett 36:5811; (c) Zorn C, Anichini B, Goti A, Brandi A, Kozhushkov SI, de Meijere A, Citti L (1999) J Org Chem 64: in press
Review: Yamada K, Ojika M, Kigoshi H (1998) Angew Chem 110:1918; Angew Chem Int Ed Engl 37:1818
Fitjer L (1982) Chem Ber 116:1047
Erden I, de Meijere A, Rousseau G, Conia J-M (1980) Tetrahedron Lett 21:2501
Weber W, Behrens U, de Meijere A (1980) Chem Ber 114:1196
Maercker A, Klein K-D (1991) J Organomet Chem 410:C35
Kaufmann D, de Meijere A (1979) Tetrahedron Lett 779
(a) Becker H (1996) Dissertation, Universität Göttingen; (b) Becker H, de Meijere A unpublished results
Bräse S (1996) Dissertation, Universität Göttingen
Bräse S, de Meijere A (1995) Angew Chem 107:2741; Angew Chem Int Ed Engl 34:2545
(a) de Meijere A, Nüske H, Es-Sayed M, Schroen M, Bräse S (1999) Angew Chem 111: in press; Angew Chem Int Ed Engl 38: in press; (b) Nüske H, Bräse S, Kozhushkov SI, de Meijere A (1999) Chem Eur J in preparation
Pohlmann T, de Meijere A (unpublished results)
Binger P, Wedemann P, Kozhushkov SI, de Meijere A (1998) Eur J Org Chem 113
O’Donnell MJ, Polt RL (1982) J Org Chem 47:2633
Hayashi T, Konishi M, Kobori Y, Kumada M, Higuchi T, Hirotsu K (1984) J Am Chem Soc 106:158
Brandl M, Kozhushkov SI, Bräse S, de Meijere A (1998) Eur J Org Chem 453
Review: Lipshutz BH (1990) Synlett 119
O’Donnell MJ, Bennett WD, Polt RL (1985) Tetrahedron Lett 26:695
Kozhushkov SI, Brandl M, Yufit DS, Machinek R, de Meijere A (1997) Liebigs Ann/Recueil 2179
Foerstner J, Kozhushkov SI, Binger P, Wedemann P, de Meijere A, Butenschön H (1998) J Chem Soc Chem Commun 239
Hofmann P, de Meijere A unpublished results
von Seebach M, Kozhushkov SI, Boese R, Yufit DS, de Meijere A unpublished results
Baldwin JE, Adlington RM, Bebbington D, Russel AT (1994) Tetrahedron 50:12015 and references cited therein
Li K, Du W, Que NLS, Liu H-w (1996) J Am Chem Soc 118:8763
(a) Yoshida M, Ezaki M, Hashimoto M, Yamashita M, Shigematsu N, Okuhara M, Kohsaka M, Horikoshi K (1990) J Antibiotics 748; (b) Kou MS, Zielinski RJ, Cialdella JI, Maschke CK (1995) J Am Chem Soc 117:10629
(a) Barrett AGM, Tustin GJ (1995) J Chem Soc Chem Commun 355; (b) Barrett AGM, Kasdorf K, Tustin GJ, Williams DJ (1995) J Chem Soc Chem Commun 1143 and references cited therein; (c) Barrett AGM, Kasdorf K (1996) J Am Chem Soc 118:11030; (d) Barrett AGM, Doubleday WW, Kasdorf K, Tustin GJ (1996) J Org Chem 61:3280; (e) Barrett AGM, Gross T, Hamprecht D, Ohkubo M, White AJP, Williams DJ (1998) Synthesis 490; (f) Barrett AGM, Hamprecht D, White AJP, Williams DJ (1997) J Am Chem Soc 119:8608
(a) Charette AB, Juteau H (1994) J Am Chem Soc 116:2651; (b) Charette AB, Prescott S, Brochu C (1995) J Org Chem 60:1081
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de Meijere, A., Kozhushkov, S.I., Khlebnikov, A.F. (2000). Bicyclopropylidene — A Unique Tetrasubstituted Alkene and a Versatile C6-Building Block. In: de Meijere, A. (eds) Small Ring Compounds in Organic Synthesis VI. Topics in Current Chemistry, vol 207. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48255-5_3
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