Abstract
The photochemical decomposition of diazoalkanes is an important route to the formation of a reactive species R—C—R which has in the literature been referred to as carbene (1a) and as methylene (1b) (in the case of R = H).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
J. Hine: Divalent Carbon. New York: Ronald 1964.
W. Kirmse: Carbene Chemistry. New York: Academic Press 1964.
W. B. De More and S. W. Benson, in: Adv. Photochem., ed. by W. A. Noyes, G. S. Hammond and J. N. Pitts jr., Vol. 2, 219–261 (1964). New York: Interscience.
H. M. Frey, in: Progress in Reaction Kinetics, ed. by G. Porter, Vol. 2, 131–164 (1964). Oxford etc.: Pergamon.
J. A. Bell, in: Progress in Physical Organic Chemistry, ed. by S. G. Cohen, A. Streitwieser jr. and R. W. Taft, Vol. 2, 1–61 (1964). New York: Interscience.
G. von Bünau, P. Potzinger and G. O. Schenck: Tetrahedron 21, 1293 (1965).
A. Ledwith: Royal Inst. Chem. Lecture Series 1964, No. 5.
W. von E. Doering and P. LaFlamme: J. Amer. chem. Soc. 78, 5447 (1956).
P. S. Skell and R. C. Woodworth: J. Amer. chem. Soc. 78, 4496 (1956).
C. D. Gutsche, G. L. Bachman and R. S. Coffey: Tetrahedron 18, 617 (1962).
G. L. Closs and R. A. Moss: J. Amer. chem. Soc. 86, 4042 (1964).
R. M. Etter, H. S. Skovronek and P. S. Skell: J. Amer. chem. Soc. 81, 1008 (1959).
W. von E. Doering and T. Mole: Tetrahedron 10, 65 (1960).
W. von E. Doering, R. G. Buttery, R. G. Laughlin and N. Chaudhuri: J. Amer. chem. Soc. 78, 3224 (1956).
H. Nozaki, R. Noyori and K. Sisido: Tetrahedron 20, 1125 (1964).
K. R. Kopecky, G. S. Hammond and P. A. Leermakers: J. Amer. chem. Soc. 84, 1015 (1962).
E. J. Moriconi and J. J. Murray: J. Org. Chem. 29, 3577 (1964).
W. von E. Doering and L. H. Knox: J. Amer. chem. Soc. 72, 2505 (1950).
W. von E. Doering and L. H. Knox: J. Amer. chem. Soc. 75, 297 (1953).
H. Meerwein, H. Disselnkötter, F. Rappen, H. von Rintelen and H. van de Vloed: Liebigs Ann. Chem. 604, 151 (1957).
S. J. Rhoads, in: Molecular Rearrangements, ed. by P. de Mayo, Vol. 1, 655–706, esp. p. 700–703 (1963). New York: Interscience.
W. von E. Doering, G. Laber, R. Vonderwahl, N. F. Chamberlain and R. B. Williams: J. Amer. chem. Soc. 78, 5448 (1956).
G. O. Schenck and H. Ziegler: Liebigs Ann. Chem. 584, 221 (1954).
K. Alder and P. Schmitz: Chem. Ber. 86, 1539 (1953).
W. von E. Doering, J.R. Mayer and C. H. DePuy: J. Amer. chem. Soc. 75, 2386 (1953).
C. D. Gutsche and H. E. Johnson: J. Amer. chem. Soc. 77, 5933 (1955).
G. O. Schenck and R. Steinmetz: Liebigs Ann. Chem. 668, 19 (1963).
J. C. Sheehan and I. Lengyel: J. Org. Chem. 28, 3252 (1963).
G. L. Closs, L. E. Closs and W. A. Böll: J. Amer. chem. Soc. 85, 3796 (1963).
G. L. Closs and W. Böll: Angew. Chem. 75, 640 (1963); intern. ed. 2, 399 (1963).
E. Müller, A. Moosmayer and A. Rieker: Z. Naturforsch. 18b, 982 (1963).
W. Schlenk: Liebigs Ann. Chem. 394, 178 (1912), esp. p. 183.
W. H. Urry and J. R. Eiszner: J. Amer. chem. Soc. 74, 5822 (1952).
W. H. Urry and N. Bilow: J. Amer. chem. Soc. 86, 1815 (1964).
W. H. Urry and J. W. Wilt: J. Amer. chem. Soc. 76, 2594 (1954).
A. N. Nesmeyanov, R. Kh. Freidlina, V. N. Kost and M. Ya. Khorlina: Tetrahedron 16, 94 (1961).
E. S. Gould: Mechanismus und Struktur in der organischen Chemie. 2. Ed., esp. p. 923–924, ref. 193 b. Weinheim: Verlag Chemie 1964.
D. W. Setser, R. Littrell and J. C. Hassler: J. Amer. chem. Soc. 87, 2062 (1965).
H. Meerwein, H. Rathjen and H. Werner: Ber. dtsch. chem. Ges. 75, 1610 (1942).
W. von E. Doering, L. H. Knox and M. Jones jr.: J. Org. Chem. 24, 136 (1959).
D. B. Richardson, M. C. Simmons and I. Dvoretzky: J. Amer. chem. Soc. 83, 1934 (1961).
W. Kirmse, L. Horner and H. Hoffmann: Liebigs Ann. Chem. 614, 19 (1958).
W. G. Dauben and F. G. Willey: J. Amer. chem. Soc. 84, 1497 (1962).
D. M. Lemal and A. J. Fry: J. Org. Chem. 29, 1673 (1964).
D. B. Denney and P. P. Klemchuk: J. Amer. chem. Soc. 80, 3289 (1958).
D. G. Farnum and P. Yates: J. Amer. chem. Soc. 84, 1399 (1962).
R. Fields and R. N. Haszeldine: Proc. Chem. Soc. 1960, 22.
R. Fields and R. N. Haszeldine: J. Chem. Soc. 1964, 1881.
H. E. Zimmerman and D. H. Paskovich: J. Amer. chem. Soc. 86, 2149 (1964).
H. M. Frey: J. Chem. Soc. 1962, 2293.
H. M. Frey and I. D. R. Stevens: J. Chem. Soc. 1963, 3514.
P. D. Bartlett and T. G. Traylor: J. Amer. chem. Soc. 84, 3408 (1962).
R. Huisgen: Angew. Chem. 75, 604 (1963), esp. p. 631; intern. Ed. 2, 565 (1963).
H. M. Frey: Pure Appl. Chem. 9, 527 (1964).
R. A. Mitsch: J. Heterocycl. Chem. 1, 59 (1964).
R. A. Mitsch: J. Heterocycl. Chem. 1, 233 (1964).
F. Misani, L. Speers and A. M. Lyon: J. Amer. chem. Soc. 78, 2801 (1956).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1968 Springer-Verlag Berlin · Heidelberg
About this chapter
Cite this chapter
Schönberg, A. (1968). Light-induced reactions of diazoalkanes, diazirines and related compounds. In: Preparative Organic Photochemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87918-0_31
Download citation
DOI: https://doi.org/10.1007/978-3-642-87918-0_31
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-87920-3
Online ISBN: 978-3-642-87918-0
eBook Packages: Springer Book Archive