Reactions of Unsaturated Azides; Part 27: [¹] Synthesis of 1,4-Diazidobuta-1,3-dienes

Abstract

Three different methods to prepare 1,4-diazidobuta-1,3-dienes are presented: nucleophilic substitution of electron-poor dichlorinated substrates, nucleophilic addition of hydrazoic acid at an electron-deficient diallene, and a sequence of prototropic isomerizations of propargyl sulfones followed by nucleophilic additions. In all cases, isolation and assignment of the diastereomeric products was possible, and some sequential reactions, such as reduction or 1,3-dipolar cycloaddition of the azido groups, were performed.

allenes - alkynes - azides - cycloaddition - dienes - isomerisation - nucleophilic addition - nucleophilic substitution

References

<A NAME="RT23411SS-1">1</A> For part 26, see: Firdous S. Banert K. Auer AA. Chem. Eur. J.  2011,  17 , in press

For reviews on vinyl azides, see:

<A NAME="RT23411SS-2A">2a</A> Banert K. In Houben-Weyl   Vol. E15:  Kropf H. Schaumann E. Thieme; Stuttgart: 1993.  p.818-875  

<A NAME="RT23411SS-2B">2b</A> Hassner A. In Azides and Nitrenes   Scriven EFV. Academic Press; Orlando: 1984.  p.35-76  

<A NAME="RT23411SS-2C">2c</A> Banert K. In Organic Azides: Syntheses and Applications   Bräse S. Banert K. Wiley; Chichester: 2010.  p.115-166  

<A NAME="RT23411SS-2D">2d</A> Collier SJ. In Science of Synthesis   Vol. 33:  Molander GA. Thieme; Stuttgart: 2006.  p.541-563  

<A NAME="RT23411SS-2E">2e</A> Smolinsky G. Pryde CA. In The Chemistry of the Azido Group   Patai S. Wiley; New York: 1971.  p.555-585  

<A NAME="RT23411SS-3A">3a</A> Padwa A. Blacklock TJ. Carlsen PHJ. Pulwer M. J. Org. Chem.  1979,  44:  3281 

<A NAME="RT23411SS-3B">3b</A> Padwa A. Smolanoff J. Tremper A. J. Org. Chem.  1976,  41:  543 

<A NAME="RT23411SS-4">4</A> Hassner A. Levy LA. J. Am. Chem. Soc.  1965,  87:  4203 

<A NAME="RT23411SS-5">5</A> For a review, see: Hassner A. Acc. Chem. Res.  1971,  4:  9 

<A NAME="RT23411SS-6">6</A> Hassner A. Keogh J. Tetrahedron Lett.  1975,  1575 

<A NAME="RT23411SS-7A">7a</A> Banert K. Köhler F. Angew. Chem. Int. Ed.  2001,  40:  174 ; Angew. Chem. 2001, 113, 173

<A NAME="RT23411SS-7B">7b</A> Banert K. Grimme S. Herges R. Heß K. Köhler F. Mück-Lichtenfeld C. Würthwein E.-U. Chem. Eur. J.  2006,  12:  7467 

<A NAME="RT23411SS-8">8</A> Gallagher TC. Storr RC. Tetrahedron Lett.  1981,  22:  2905 

<A NAME="RT23411SS-9A">9a</A> Farmer EH. J. Chem. Soc., Trans.  1923,  123:  2531 

<A NAME="RT23411SS-9B">9b</A> Baeyer A. Rupe H. Justus Liebigs Ann. Chem.  1890,  256:  1 

<A NAME="RT23411SS-10A">10a</A> Treibs W. Walther H. Chem. Ber.  1955,  88:  396 

<A NAME="RT23411SS-10B">10b</A> Roeding A. Kiepert K. Chem. Ber.  1955,  88:  733 

<A NAME="RT23411SS-10C">10c</A> Treibs W. Zimmermann G. Chem. Ber.  1957,  90:  1146 

<A NAME="RT23411SS-11">11</A>

The trans,trans structure of the higher-melting diastereoisomer of 7 was discussed,^¹² and the crystal and molecular structure of dimethyl trans,trans-2,5-dichloro-muconate was determined by single-crystal X-ray diffraction techniques.^¹³ In the latter case, however, neither the melting point nor other information on 7 including the method used to prepare this compound were given. Thus, the found (Z,Z)-configuration could not be assigned to the substances depicted in Scheme  [²] .

<A NAME="RT23411SS-12">12</A> Takei S. Nakajima M. Tomida I. Chem. Ber.  1956,  89:  263 

<A NAME="RT23411SS-13">13</A> Einspahr H. Donohue J. Acta Crystallogr., Sect. B: Struct. Sci.  1973,  29:  1875 

<A NAME="RT23411SS-14A">14a</A> Vögeli U. von Philipsborn W. Org. Magn. Reson.  1975,  7:  617 

<A NAME="RT23411SS-14B">14b</A> Braun S. Org. Magn. Reson.  1978,  11:  197 

<A NAME="RT23411SS-15A">15a</A> Nesmeyanov AN. Rybinskaya MI. Kelekhsaeva TG. J. Org. Chem. USSR (Engl. Transl.)  1968,  4:  897 

<A NAME="RT23411SS-15B">15b</A> Rybinskaya MI. Nesmeyanov AN. Kochetkov NK. Russ. Chem. Rev. (Engl. Transl.)  1969,  38:  433 

<A NAME="RT23411SS-16">16</A> For another example of configuration change due to the formation of the thermodynamically favored vinyl azide, see: Jonas J. Mazal C. Rappoport Z. J. Phys. Org. Chem.  1994,  7:  652 

<A NAME="RT23411SS-17">17</A> Tietze LF. Eicher T. Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium   Thieme; Stuttgart: 1991.  p.40 

<A NAME="RT23411SS-18">18</A> Cai B.-z. Blackburn GM. Synth. Commun.  1997,  27:  3943 

<A NAME="RT23411SS-19A">19a</A> Palacios F. Aparicio D. de los Santos JM. Perez de Heredia I. Rubiales G. Org. Prep. Proced. Int.  1995,  27:  171 

<A NAME="RT23411SS-19B">19b</A> Fendel W. Dissertation   TU Chemnitz; Germany: 1997. 

<A NAME="RT23411SS-19C">19c</A> Duncan M. Gallagher MJ. Org. Magn. Reson.  1981,  15:  37 

<A NAME="RT23411SS-20">20</A> Thyagarajan BS. Glaspy PE. Baker E. Org. Mass Spectrom.  1980,  15:  224 

<A NAME="RT23411SS-21">21</A> For a review on acceptor-substituted allenes, see: Banert K. Lehmann J. In Modern Allene Chemistry   Krause N. Hashmi ASK. Wiley-VCH; Weinheim: 2004.  p.359 

<A NAME="RT23411SS-22">22</A> Organic Azides: Syntheses and Applications   Bräse S. Banert K. John Wiley & Sons Ltd.; Chichester: 2010. 

<A NAME="RT23411SS-23">23</A> Sheldrick GM. SHELXTL Version 5.1, An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data   Siemens Analytical X-ray Instruments; Madison WI: 1990.