Manchester United’s late attempt to finalise David de Gea’s transfer to Real Madrid ended in chaos and finger-pointing on Monday night when the paperwork was not signed off in time at the end of a hectic and sometimes baffling day of transfer movement that also saw the Old Trafford club make Monaco’s Anthony Martial the most expensive teenager in world football.

De Gea’s paperwork was not filed before the midnight Spanish transfer deadline, with the goalkeeper described as “distraught” about the late twist to a remarkable day in which United also moved out Adnan Januzaj and Javier Hernández. Real were working into the early hours to try to persuade the Spanish authorities to let the deal happen but, whereas there are many examples of transfers being conducted after the deadline in England, stricter rules are applied in La Liga. Real are expected to try again on Tuesday by appealing to Fifa but at 2am in Spain the deal looked as if it had collapsed and there were reports blaming United for purportedly faxing one of the documents too late.

United are adamant they prepared everything with time to spare and that the blame should not be apportioned in their direction. United have a time-stamp on the various faxes, filed through Fifa’s Transfer Matching System to validate it was not their fault and clearly think Real are culpable for waiting so long to arrange a transfer that has been in the offing for several months.

Real, however, insist United are responsible and claim they received a vital fax at 11.59pm, leaving them with no time to submit it to the Liga de Fútbol Profesional. The document is understood to have been forwarded a minute past the deadline and, as such, De Gea was informed that the two clubs would have to abort the £29.3m player-plus-cash exchange involving Keylor Navas that had been agreed during the day.

That deal valued De Gea around £22m after United abandoned their original asking price of £33m in the face of Real’s deliberate negotiating tactic to leave it as late as possible. United had previously maintained they would not sell their goalkeeper and player of the year unless they received a record transfer fee for a goalkeeper – exceeding the £32.6m that Juventus paid for Gianluigi Buffon in 2001 – but with only hours remaining until the Spanish transfer window closed, Madrid’s offer was considered better than the alternative of De Gea leaving as a free agent next summer.

Real’s tactic now appears to have backfired on them logistically because, even though the two clubs started talking on Monday morning, United were also involved in several other major pieces of business rather than devoting all their attention to one deal.

The most significant of them was the £36m deal for the 19-year-old Martial, with potential add-ons that could eventually take it above £50m, in another demonstration of the club’s extraordinary spending power. Martial is regarded as one of the more exciting young talents in French football, likened by some observers to a young Thierry Henry, but the price has surprised many of his admirers at other clubs. Tottenham had tried to sign him earlier in the summer for less than half of what United have paid and, for all the teenager’s potential, the shift in personnel represents a considerable gamble for his new club given that Wayne Rooney is now the only senior striker in Louis van Gaal’s squad.

Hernández has been sold to Bayer Leverkusen for £7.3m, despite Van Gaal stating two weeks ago that the Mexican would not be transferred, and Januzaj’s season-long loan at Borussia Dortmund means United’s attacking options have been diminished, rather than strengthened, unless there is another addition on Tuesday, the final day of the British window. If not, United will be more reliant than ever on Rooney, who turns 30 in October and has struggled to impress so far this season, apart from his hat-trick performance in the Champions League qualifying tie against Bruges last week.

Martial made 48 appearances for Monaco last season, scoring 12 goals, and started playing as a central striker from March onwards. The teenager is a product of Lyon’s academy and moved to Monaco two years ago for an initial £3.5m. As part of that deal Lyon are due a percentage, thought to be as much as 25%, of any profit Monaco make on future transfers.

The swiftness of that deal contrasts wildly with the summer-long saga involving De Gea and it is a measure of Real’s negotiating ploys that the proposal involving Navas, lodged early on Monday, was their first official bid of the entire process.

United had tried earlier in the summer to arrange a player-plus-cash exchange with Gareth Bale only to receive no encouragement from the Real president, Florentino Perez, and then switched their attention to Sergio Ramos, an episode that finished with the defender signing a new contract at the Bernabéu and being awarded the club captaincy.

Real’s delaying tactics caused intense irritation at Old Trafford and had looked like being successful, capitalising on the fact that United would otherwise have been left with an unhappy goalkeeper who would have been worth nothing to them next summer.

United, in turn, agreed to take on the 28-year-old Navas, even though there is a clear sense in Madrid that he is not ideally suited to English football. Navas joined Madrid in a £7m move from Levante last year and is regarded as a fine shot-stopper but vulnerable to crosses and, at 6ft, shorter than most of the goalkeepers in the Premier League. United’s thinking was swayed by Sergio Romero’s erratic form during the early weeks of the season but the proposed De Gea deal still represented a climbdown, having previously stated there was no way they would let Real dictate the process.

Januzaj’s move to Dortmund reflects how he has fallen out of favour at Old Trafford in the Van Gaal era and a chaotic day at Old Trafford also saw the back-up goalkeeper Anders Lindegaard follow the same route as Darren Fletcher and Jonny Evans to become the latest United player to join West Bromwich Albion.